Compound for organic electric element, organic electric element using same, and electronic device comprising same organic electronic element

ABSTRACT

Use of a mixture of compounds according to the present invention as a phosphorescent host material can achieve a high light emitting efficiency and a low driving voltage in an organic electric element. In addition, an organic electric element having a greatly improved lifespan, and an electronic device comprising the same are provided.

BACKGROUND Technical Field

The present invention relates to compound for organic electronicelement, organic electronic element using the same, and an electronicdevice thereof.

Background Art

In general, organic light emitting phenomenon refers to a phenomenonthat converts electronic energy into light energy by using an organicmaterial.

An organic electronic element using an organic light emitting phenomenonusually has a structure including an anode, a cathode, and an organicmaterial layer interposed therebetween. Here, in order to increase theefficiency and stability of the organic electronic element, the organicmaterial layer is often composed of a multi-layered structure composedof different materials, and for example, may include a hole injectionlayer, a hole transport layer, an emitting layer, an electron transportlayer, an electron injection layer and the like.

A material used as an organic material layer in an organic electronicelement may be classified into a light emitting material and a chargetransport material, such as a hole injection material, a hole transportmaterial, an electron transport material, an electron injection materialand the like depending on its function.

In the case of a polycyclic compound containing a heteroatom, thedifference in properties according to the material structure is so largethat it is applied to various layers as a material of an organicelectronic element. In particular, it has characteristics of differentband gaps (HOMO, LUMO), electronical characteristics, chemicalproperties, and physical properties depending on the number of rings,fused positions and the type and arrangement of heteroatoms, thereforeapplication development for layers of various organic electronicelements using the same has been progressed.

As a representative example thereof, in the following Patent Documents 1to 4, the performance of the 5-membered cyclic compound in thepolycyclic compound has been reported depending on the hetero type,arrangement, substituent type, fused position, and the like.

[Patent Document 1]: U.S. Pat. No. 5,843,607

[Patent Document 2]: Japanese Laid-Open Patent Publication No.1999-162650

[Patent Document 3]: Korean Published Patent Application No.2008-0085000

[Patent Document 4]: US Patent Publication No. 2010-0187977

[Patent Document 5]: Korean Published Patent Application No.2011-0018340

[Patent Document 6]: Korean Published Patent Application No.2009-0057711

Patent Documents 1 and 2 disclose an embodiment in which theindolecarbazole core in which the hetero atom in the 5-membered cycliccompound is composed only of nitrogen (N) is used, and an aryl groupsubstituted or unsubstituted in N of indolocarbazole is used. However,in the prior invention 1, there exists only a simple aryl groupsubstituted or unsubstituted with an alkyl group, an amino group, analkoxy group, or the like as a substituent, so that the effect of thesubstituents of the polycyclic compounds was very poor to prove, andonly the use as a hole transport material is described, and the usethereof as a phosphorescent host material is not described.

Patent Documents 3 and 4 disclose a compound in which pyridine,pyrimidine, triazine or the like containing an aryl group and N,respectively, were substituted for an indolecarbazole core having ahetero atom N in the same 5-membered cyclic compound as in the abovePatent Documents 1 and 2, however only the use examples forphosphorescent green host materials are described, and the performancefor other heterocyclic compounds substituted for indolecarbazole core isnot described.

In Patent Documents 5, Nitrogen (N), oxygen (O), sulfur (S), carbon andthe like are described as heteroatom in the 5-membered cyclic compound,however there are only examples using the same heteroatom in theperformance measurement data, the performance characteristics of a5-membered cyclic compound containing a different heteroatom could notbe confirmed.

Therefore, the patent document does not disclose solutions to low chargecarrier mobility and low oxidation stability of a 5-membered cycliccompound containing same heteroatom.

When the 5-membered cyclic compound molecules are generally laminated,as the adjacent π-electrons increase, they have a strong electronicalinteraction, and this is closely related to the charge carrier mobility,particularly, the same 5-membered cyclic compound of N—N type has anedge-to-face morphology as an order of arrangement of molecules whenmolecules are laminated, otherwise a different 5-membered cycliccompound with different heteroatoms has an antiparallel cofacialπ-stacking structure in which the packing structure of the molecules isopposite to each other, so that the arrangement order of the moleculesbecomes face-to-face morphology. It is reported that the steric effectof the substituent substituted on the asymmetrically arranged heteroatom N as the cause of this laminated structure causes relatively highcarrier mobility and high oxidation stability (Org. Lett. 2008, 10,1199).

In Patent Document 6, an example of using as a fluorescent host materialfor various polycyclic compounds having 7 or more membered cycliccompounds has been reported.

As described above, the fused positions, the number of rings, thearrangement of heteroatoms, and characteristic change by type of thepolycyclic compounds have not yet been sufficiently developed.

Particularly, in a phosphorescent organic electronic element using aphosphorescent dopant material, the LUMO and HOMO levels of the hostmaterial have a great influence on the efficiency and life span of theorganic electronic element, this is because the charge balance controlin the emitting layer, the quenching of the dopant, and the reduction inefficiency and life span due to light emission at the interface of thehole transport layer can be prevented, depending on whether electron andhole injection in the emitting layer can be efficiently controlled.

For fluorescent and phosphorescent host materials, recently we have beenstudying the increase of efficiency and life span of organic electronicelements using TADF (thermal activated delayed fluorescent), exciplex,etc., particularly, and many studies have been carried out to identifythe energy transfer method from the host material to the dopantmaterial.

Although there are various methods for identifying the energy transferin the emitting layer for TADF (thermally activated delayed fluorescent)and exciplex, it can be easily confirmed by the PL lifetime (TRTP)measurement method.

The TRTP (Time Resolved Transient PL) measurement method is a method ofobserving a decay time over time after irradiating the host thin filmwith a pulsed light source, and therefore it is possible to identify theenergy transfer method by observing the energy transfer and the lagtime. The TRTP measurement can distinguish between fluorescence andphosphorescence, an energy transfer method in a mixed host material, anexciplex energy transfer method, and a TADF energy transfer method.

There are various factors affecting the efficiency and life spandepending on the manner in which the energy is transferred from the hostmaterial to the dopant material, and the energy transfer method differsdepending on the material, so that the development of stable andefficient host material for organic electronic element has not yet beensufficiently developed. Therefore, development of new materials iscontinuously required, and especially development of a host material foran emitting layer is urgently required.

DETAILED DESCRIPTION OF THE INVENTION Summary

The present invention has been proposed in order to solve the problemsof the phosphorescent host material, and an object of the presentinvention is, by controlling the HOMO level of a host material of aphosphorescent emitting organic electronic element including aphosphorescent dopant, to provide a compound capable of controllingcharge balance and of improving efficiency and life span in an emittinglayer, and an organic electronic element using the same and anelectronic device thereof.

Technical Solution

In order to control the efficient hole injection in the emitting layerof the phosphorescence emitting organic electronic element, bycontaining a specific second host material in combination with aspecific first host material as a main component, it is possible toreduce the energy barrier of the emitting layer and the adjacent layer,the charge balance in the emitting layer is maximized, thereby providinghigh efficiency and high life of the organic electronic device.

The present invention provides an organic electronic element comprisinga first electrode, a second electrode, and an organic material layerformed between the first electrode and the second electrode, wherein theorganic material layer includes an emitting layer, wherein the emittinglayer includes a first host compound represented by the followingFormula (1) and a second host compound represented by the followingFormula (2).

In another aspect, the present invention also provides an organicelectronic element using the compound represented by the above Formulasand an electronic device thereof.

Effects of the Invention

By using the mixture according to the present invention as aphosphorescent host material, it is possible to achieve a high luminousefficiency and a low driving voltage of an organic electric element, andthe life span of the device can be greatly improved.

BRIEF DESCRIPTION OF THE DRAWINGS

The FIGURE is an illustration of an organic electroluminescent deviceaccording to the present invention.

100: organic electric element, 110: substrate 120: the firstelectrode(anode), 130: the hole injection layer 140: the hole transportlayer, 141: a buffer layer 150: the emitting layer, 151: the emittingauxiliary layer 160: the electron transport layer, 170: the electroninjection layer 180: the second electrode(cathode)

DETAILED DESCRIPTION

Hereinafter, some embodiments of the present invention will be describedin detail. Further, in the following description of the presentinvention, a detailed description of known functions and configurationsincorporated herein will be omitted when it may make the subject matterof the present invention rather unclear.

In addition, terms, such as first, second, A, B, (a), (b) or the likemay be used herein when describing components of the present invention.Each of these terminologies is not used to define an essence, order orsequence of a corresponding component but used merely to distinguish thecorresponding component from other component(s). It should be noted thatif a component is described as being “connected”, “coupled”, or “linked”to another component, the component may be directly connected orconnected to the other component, but another component may be“connected”, “coupled” or “linked” between each component.

As used in the specification and the accompanying claims, unlessotherwise stated, the following is the meaning of the term as follows.

Unless otherwise stated, the term “halo” or “halogen”, as used herein,includes fluorine, bromine, chlorine, or iodine.

Unless otherwise stated, the term “alkyl” or “alkyl group”, as usedherein, has a single bond of 1 to 60 carbon atoms, and means saturatedaliphatic functional radicals including a linear alkyl group, a branchedchain alkyl group, a cycloalkyl group (alicyclic), an cycloalkyl groupsubstituted with a alkyl or an alkyl group substituted with acycloalkyl.

Unless otherwise stated, the term “haloalkyl” or “halogen alkyl”, asused herein, includes an alkyl group substituted with a halogen.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl substituted one or more of carbon atoms consisting of an alkylwith hetero atom.

Unless otherwise stated, the term “alkenyl” or “alkynyl”, as usedherein, has double or triple bonds of 2 to 60 carbon atoms, but is notlimited thereto, and includes a linear or a branched chain group.

Unless otherwise stated, the term “cycloalkyl”, as used herein, meansalkyl forming a ring having 3 to 60 carbon atoms, but is not limitedthereto.

Unless otherwise stated, the term “alkoxyl group”, “alkoxy group” or“alkyloxy group”, as used herein, means an oxygen radical attached to analkyl group, but is not limited thereto, and has 1 to 60 carbon atoms.

Unless otherwise stated, the term “alkenoxyl group”, “alkenoxy group”,“alkenyloxyl group” or “alkenyloxy group”, as used herein, means anoxygen radical attached to an alkenyl group, but is not limited thereto,and has 2 to 60 carbon atoms.

Unless otherwise stated, the term “aryloxyl group” or “aryloxy group”,as used herein, means an oxygen radical attached to an aryl group, butis not limited thereto, and has 6 to 60 carbon atoms.

Unless otherwise stated, the term “aryl group” or “arylene group”, asused herein, has 6 to 60 carbon atoms, but is not limited thereto.Herein, the aryl group or arylene group means a monocyclic andpolycyclic aromatic group, and may also be formed in conjunction with anadjacent group. Examples of “aryl group” may include a phenyl group, abiphenyl group, a fluorene group, or a spirofluorene group.

The prefix “aryl” or “ar” means a radical substituted with an arylgroup. For example, an arylalkyl may be an alkyl substituted with anaryl, and an arylalkenyl may be an alkenyl substituted with aryl, and aradical substituted with an aryl has a number of carbon atoms as definedherein.

Also, when prefixes are named subsequently, it means that substituentsare listed in the order described first. For example, an arylalkoxymeans an alkoxy substituted with an aryl, an alkoxylcarbonyl means acarbonyl substituted with an alkoxyl, and an arylcarbonylalkenyl alsomeans an alkenyl substituted with an arylcarbonyl, wherein thearylcarbonyl may be a carbonyl substituted with an aryl.

Unless otherwise stated, the term “heteroalkyl”, as used herein, meansalkyl containing one or more of hetero atoms. Unless otherwise stated,the term “heteroaryl group” or “heteroarylene group”, as used herein,means a C2 to C60 aryl containing one or more of hetero atoms or arylenegroup, but is not limited thereto, and includes at least one ofmonocyclic and polycyclic rings, and may also be formed in conjunctionwith an adjacent group.

Unless otherwise stated, the term “heterocyclic group”, as used herein,contains one or more heteroatoms, but is not limited thereto, has 2 to60 carbon atoms, includes any one of monocyclic and polycyclic rings,and may include heteroaliphatic ring and/or heteroaromatic ring. Also,the heterocyclic group may also be formed in conjunction with anadjacent group.

Unless otherwise stated, the term “heteroatom”, as used herein,represents at least one of N, O, S, P, or Si.

Also, the term “heterocyclic group” may include a ring containing SO₂instead of carbon consisting of cycle. For example, “heterocyclic group”includes compound below.

Unless otherwise stated, the term “aliphatic”, as used herein, means analiphatic hydrocarbon having 1 to 60 carbon atoms, and the term“aliphatic ring”, as used herein, means an aliphatic hydrocarbon ringhaving 3 to 60 carbon atoms.

Unless otherwise stated, the term “ring”, as used herein, means analiphatic ring having 3 to 60 carbon atoms, or an aromatic ring having 6to 60 carbon atoms, or a hetero ring having 2 to 60 carbon atoms, or afused ring formed by the combination of them, and includes a saturatedor unsaturated ring.

Other hetero compounds or hetero radicals other than the above-mentionedhetero compounds include, but are not limited thereto, one or moreheteroatoms.

Unless otherwise stated, the term “carbonyl”, as used herein, isrepresented by —COR′, wherein R′ may be hydrogen, an alkyl having 1 to20 carbon atoms, an aryl having 6 to 30 carbon atoms, a cycloalkylhaving 3 to 30 carbon atoms, an alkenyl having 2 to 20 carbon atoms, analkynyl having 2 to 20 carbon atoms, or the combination of these.

Unless otherwise stated, the term “ether”, as used herein, isrepresented by —R—O—R′, wherein R or R′ may be independently hydrogen,an alkyl having 1 to 20 carbon atoms, an aryl having 6 to 30 carbonatoms, a cycloalkyl having 3 to 30 carbon atoms, an alkenyl having 2 to20 carbon atoms, an alkynyl having 2 to 20 carbon atoms, or thecombination of these.

Unless otherwise stated, the term “substituted or unsubstituted”, asused herein, means that substitution is substituted by at least onesubstituent selected from the group consisting of, but is not limitedthereto, deuterium, halogen, an amino group, a nitrile group, a nitrogroup, a C₁-C₂₀ alkyl group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkylaminegroup, a C₁-C₂₀ alkylthiopen group, a C₆-C₂₀ arylthiopen group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₃-C₂₀ cycloalkyl group, aC₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted by deuterium, aC₈-C₂₀ arylalkenyl group, a silane group, a boron group, a germaniumgroup, and a C₂-C₂₀ heterocyclic group.

Unless otherwise expressly stated, the Formula used in the presentinvention, as used herein, is applied in the same manner as thesubstituent definition according to the definition of the exponent ofthe following Formula.

Wherein, when a is an integer of zero, the substituent R¹ is absent, andwhen a is an integer of 1, the sole substituent R¹ is linked to any oneof the carbon constituting the benzene ring, and when a is an integer of2 or 3, they are respectively combined as follows, wherein R¹ may be thesame or different from each other. When a is an integer from 4 to 6, itis bonded to the carbon of the benzene ring in a similar manner, whilethe labeling of the hydrogen bonded to the carbon forming the benzenering is omitted

Unless otherwise expressly stated, the terms “ortho”, “meta”, and “para”used in the present invention refer to the substitution positions of allsubstituents, and the ortho position indicates the position of thesubstituent immediately adjacent to the compound, for example, whenbenzene is used, it means 1 or 2 position, and the meta position is thenext substitution position of the neighbor substitution position, whenbenzene as an example stands for 1 or 3 position, and the para positionis the next substitution position of the meta position, which means 1and 4 position when benzene is taken as an example. A more detailedexample of the substitution position is as follows, and it can beconfirmed that the ortho-, and meta-position are substituted bynon-linear type and para-positions are substituted by linear type.

[Example of Ortho-Position]

[Example of Meta-Position]

[Example of Para-Position]

Hereinafter, a compound according to an aspect of the present inventionand an organic electric element comprising the same will be described.

The present invention provides an organic electric element comprising afirst electrode, a second electrode, and an organic material layerformed between the first electrode and the second electrode, wherein theorganic material layer comprises an emitting layer, wherein the emittinglayer comprises a first host compound represented by Formula (1) and asecond host compound represented by Formula (2) as a phosphorescentlight emitting layer.

{in Formulas (1) and (2),1) Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are each independently selected from thegroup consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one hetero atom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b)); and Ar¹ and Ar² or Ar³ and Ar⁴ may be bonded toeach other to form a ring,2) c and e are an integer of 0 to 10, and d is an integer of 0 to 2,3) R³, R⁴ and R⁵ are the same or different from each other, and are eachindependently selected from the group consisting of hydrogen; deuterium;halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si or P; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; aC₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));or in case c, d and e are 2 or more, and R³, R⁴ and R⁵ are each inplural being the same or different, and a plurality of R³ or a pluralityof R⁴ or a plurality of R⁵ may be bonded to each other to form a ring.4) L¹, L², L³, L⁴, L⁵ and L⁶ are each independently selected from thegroup consisting of a single bond; a C₆-C₆₀ arylene group; and afluorenylene group; a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group; provided thatexcept when L⁵ is a single bond,5) A and B are each independently a C₆-C₂₀ aryl group or a C₂-C₂₀heterocyclic group, provided that when both A and B are a substituted orunsubstituted C₆ aryl group (phenyl group), d is 2, and R⁴s are bondedto each other to form an aromatic or heterocyclic group,6) i and j are 0 or 1, with the proviso that i+j is 1 or more, and wheni or j is 0, it means a direct bond,7) X¹ and X² are each independently N-L⁷-Ar⁶, O, S, or CR⁶R⁷;wherein L⁷ is the same as L¹ to L⁴ or L⁶, wherein Ar⁶ is the same as Ar¹to Ar⁵,wherein R⁶ and R⁷ are each independently hydrogen; a C₆-C₆₀ aryl group;a fluorenyl group; a C₂-C₆₀ heterocyclic group; or a C₁-C₅₀ alkyl group;wherein R⁶ and R⁷ may combine to each other to form a spiro,8) wherein, L′ is selected from the group consisting of a single bond; aC₆-C₆₀ arylene group; a fluorenylene group; a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic; and R_(a) and R_(b) are each independently selected fromthe group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; a fusedring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and aC₂-C₆₀ heterocyclic group containing at least one hetero atom of O, N,S, Si, or P,wherein, the aryl group, fluorenyl group, arylene group, heterocyclicgroup, fluorenylene group, fused ring group, alkyl group, alkenyl group,alkoxy group and aryloxy group may be substituted with one or moresubstituents selected from the group consisting of deuterium; halogen; asilane group substituted or unsubstituted with C₁-C₂₀ alkyl group orC₆-C₂₀ aryl group; siloxane group; boron group; germanium group; cyanogroup; nitro group; -L′-N(R_(a))(R_(b)); a C₁-C₂₀ alkylthio group;C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ aryl group substituted withdeuterium; a fluorenyl group; C₂-C₂₀ heterocyclic group; C₃-C₂₀cycloalkyl group; C₇-C₂₀ arylalkyl group; and C₈-C₂₀ arylalkenyl group;wherein the substituents may combine each other and form a saturated orunsaturated ring, wherein the term ‘ring’ means C₃-C₆₀ aliphatic ring orC₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclic group or a fused ringformed by the combination of thereof and includes a saturated orunsaturated ring.}

In addition, the present invention provides the compounds represented byFormulas (1) and (2).

The present invention also provides an organic electric elementcomprising a compound represented by the following Formula (3) when Ar¹and Ar² in Formula (1) form a ring.

{In Formula (3),1) L³, L⁴, L⁵, Ar³ and Ar⁴ are the same as defined above,2) a and b are each independently an integer of 0 to 4,3) R¹ and R² are the same or different from each other, and are eachindependently selected from the group consisting of hydrogen; deuterium;halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₂₀ heterocyclicgroup including at least one heteroatom of O, N, S, Si or P; a fusedring group of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀ aromatic ring; aC₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; aC₁-C₂₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b));or in case a and b are 2 or more, R¹ and R² are each in plural being thesame or different, and a plurality of R¹ or a plurality of R² may bebonded to each other to form a ring.}

In Formula (1) of the present invention, L¹, L², L³, L⁴ and L⁵ are eachindependently any one of the following Formulas (A-1) to (A-13).

{in Formulas (A-1) to (A-13),1) a′, c′, d′ and e′ are an integer of 0 to 4; and b′ is an integer of 0to 6; and f′ and g′ are an integer of 0 to 3; and h′ is an integer of 0or 1; and i′ is an integer of 0 to 2, and j′ is an integer of 0 to 4,2) R⁸, R⁹, R¹⁰ and R¹⁵ are the same or different from each other, andare each independently selected from the group consisting of hydrogen;deuterium; halogen; a C₆-C₂₀ aryl group; a fluorenyl group; a C₂-C₂₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀ aromaticring; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₂₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b));wherein e′, f′, g′, i′ and j′ are 2 or more, R⁸, R⁹, R¹⁰ and R¹⁵ areeach in plural being the same or different, and a plurality of R⁸ or aplurality of R⁹ or a plurality of R¹⁰ or a plurality of R¹⁵, twoadjacent R⁸ and R⁹, or R⁹ and R¹⁰, or R¹⁰ and R¹⁵ may be bonded to forman aromatic ring or heteroaromatic ring,3) Y is N-L⁸-Ar⁷, O, S or CR¹¹R¹²,Wherein L⁸ is the same as L¹ to L⁶ defined above, wherein Ar⁷ is thesame as Ar¹ to Ar⁵ defined above,Wherein R¹¹ and R¹² are the same as R⁶ and R⁷ defined above,4) Z¹, Z² and Z³ are CR¹³ or N and at least one is N, and R¹³ is thesame as R⁸ and R¹⁰ defined above.}

In Formula (1), L⁵ preferably comprises a compound represented byFormula (A-10), and the present invention also provides an organicelectric device comprising the same. Formula (A-10) may be representedby the following Formulas C-1 to C-10, preferably Formulas C-2, C-3,C-4, C-6, C-7, C-9.

The first host compound represented by Formula (1) is represented by anyone of the following Formulas (3-1) to (3-3).

{In Formulas (3-1) to (3-3),R¹, R², R⁸, R⁹, a, b, a′, d′, f′, g′, L³, L⁴, Ar³ and Ar⁴ are the sameas defined above.}

The compound represented by Formula (1) of the present inventioncomprises a compound represented by the following Formula (3-4) or(3-5).

{In Formulas (3-4) and (3-5),1) Ar⁴, L³, L⁴, L⁵, R¹, R², R⁸, R⁹, a, b, f′ and g′ are the same asdefined above,2) W is the same as Y defined above.}

In one embodiment of the present invention, Ar³ and Ar⁴ in Formula (1)are all C₆-C₂₄ aryl groups, and more specifically, at least one of Ar³and Ar⁴ of Formula (1) is dibenzothiophene or dibenzofuran.

In one embodiment of the present invention, the first host compoundrepresented by Formula (1) is represented by any one of the followingFormulas (3-6) to (3-19).

{In Formulas (3-6) to (3-19),L³, L⁴, L⁵, Ar³, Ar⁴, R¹, R², a and b are the same as defined above.}

In another embodiment of the present invention, the first host compoundrepresented by Formula (1) is represented by Formulas (3-20).

{in Formula (3-20),Ar¹, Ar², Ar³, Ar⁴, L¹, L², L³, L⁴, R⁸, R⁹, f′ and g′ are the same asdefined above.}

Preferably, at least one of Ar¹, Ar², Ar³ and Ar⁴ in Formula (3-20) isdibenzothiophene or dibenzofuran.

In one embodiment of the present invention, at least one of L¹, L², L³,L⁴ and L⁵ in Formula (1) is substituted with a meta position.

In another aspect, the present invention includes a compound wherein thesecond host compound represented by Formula (2) is represented by thefollowing Formula (4) or (5).

{in Formulas (4) and (5),R³, R⁴, R⁵, L⁶, Ar⁵, X¹, X², A, B, c, d, and e are the same as definedabove.}

The present invention also comprises a compound wherein A and B inFormula (2) are selected from the group consisting of the followingFormulas (B-1) to (B-7).

{In Formulas (B-1) to (B-7),1) Z⁴ to Z⁵⁰ are CR¹⁴ or N, and R¹⁴ is the same as R¹ defined above,2) * indicates the position to be condensed.}

As another example, the present invention provides a compound whereinthe second host compound represented by Formula (2) includes a compoundrepresented by any of the following Formulas (4-1) to (4-35).

{in Formulas (4-1) to (4-35),1) X¹, X², L⁶, Ar⁵, R³, R⁴ and R⁵, are the same as defined above,2) c and e are any one of integers of 0 to 8,3) d is any one of integers of 0 to 4.}

The second host compound represented by Formula (2) comprises compoundsrepresented by the following Formulas (6-1) to (6-8).

{in Formulas (6-1) to (6-8),R³, R⁴, R⁵, R⁶, R⁷, L⁶, Ar⁵, c, d, e, A and B are the same as definedabove.}

In the above Formulas of the present invention, when Ar¹, Ar², Ar³, Ar⁴,Ar⁵, Ar⁶, Ar⁷ and R¹, R², R³, R⁴ and R⁵ are aryl groups, it ispreferably C₆-C₃₀ aryl group, more preferably C₆-C₂₄ aryl group, andwhen Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷ and R¹, R², R³, R⁴,

R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰ are heterocyclic groups, it is preferably aC₂-C₄₀ heterocyclic group, more preferably a C₂-C₃₀ heterocyclic group,still more preferably a C₂-C₂₄ heterocyclic group.

when Ar¹, Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷, and R¹, R², R³, R⁴, R⁵, R⁶, R⁷,R⁸, R⁹, R¹⁰ are aryl groups, specific examples thereof include phenyl,biphenyl, terphenyl, quaterphenyl, stylbenyl, naphthyl, anthracenyl,phenanthryl, pyrenyl, perylenyl, klycenyl group, and the like. When Ar¹,Ar², Ar³, Ar⁴, Ar⁵, Ar⁶, Ar⁷, and R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰ are heterocyclic groups, specific examples thereof include athiophene group, a furan group, a pyrrole group, an imidazole group, athiazole group, an oxazole group, an oxadiazole group, a triazole group,a pyridyl group, a bipyridyl group, a pyrimidyl group, a triazine group,a pyrazine group, a triazole group, an acridyl group, a pyridazinegroup, a pyrazinyl group, a quinolinyl group, a quinazolinyl group, aquinoxalinyl group, a benzoquinoxaline, a dibenzoquinoxaline, aphthalazinyl group, a pyridopyrimidinyl group, a pyridopyrazinyl group,a pyrazinopyrazinyl group, an isoquinoline group, an indole group, acarbazole group, indolocarbazole, acridine, phenoxazine,benzopyridazine, benzopyrimidine, carboline, benzocarboline, benzoxazolegroup, a benzoimidazole group, a benzothiazole group, a benzocarbazolegroup, a benzothiophene group, dibenzothiophene group, a benzofuranylgroup, a phenanthroline group, a thiazolyl group, an isoxazolyl group,an oxadiazolyl group, a thiadiazolyl group, a benzothiazolyl group, aphenothiazinyl group and dibenzofuranyl group, thienothiophene,benzothienopyridine, benzothienopyrimidine, benzofuropyrimidine,dimethylbenzoindenopyrimidine, phenanthrofuropyrimidine,naphthofuropyrimidine, naphthothienopyrimidine, dibenzothiophene group,thianthrene, dihydrobenzothiophenopyrazine, dihydrobenzofuropyrazine,and the like, but are not limited thereto.

Also, when L¹, L², L³, L⁴, L⁵ and L⁶ in Formula of the present inventionare an arylene group, it may preferably be an C₆-C₃₀ arylene group, morepreferably an C₆-C₈ arylene group, illustratively, it may be phenylene,biphenyl, terphenyl, naphthalene, anthracene, phenanthrene, and thelike. Preferably, L¹ is a heterocyclic group, it is preferably a C₂-C₃₀heterocyclic group, more preferably a C₂-C₁₈ heterocyclic group,illustratively, it can be dibenzofuran, dibenzothiophene, carbazole, andthe like, and when L¹ is a fluorenylene group, it can be exemplarily9,9-dimethyl-9H-fluorene.

In the present invention, the first host compound represented by Formula(1) comprises any one of the following Compounds 1-1 to 1-60 and 2-1 to2-106.

Also, in the present invention, the second host compound represented byFormula (2) comprises any one of the following Compounds 3-1 to 3-124.

Referring to the FIGURE, the organic electric element (100) according tothe present invention includes a first electrode (120) formed on asubstrate (110), a second electrode (180), and an organic material layerincluding the compound represented by Formula (1) between the firstelectrode (120) and the second electrode (180). Here, the firstelectrode (120) may be an anode (positive electrode), and the secondelectrode (180) may be a cathode (negative electrode). In the case of aninverted organic electric element, the first electrode may be a cathode,and the second electrode may be an anode.

The organic material layer may include a hole injection layer (130), ahole transport layer (140), an emitting layer (150), an electrontransport layer (160), and an electron injection layer (170) formed insequence on the first electrode (120). Here, the remaining layers exceptthe emitting layer (150) may not be formed. The organic material layermay further include a hole blocking layer, an electron blocking layer,an emitting-auxiliary layer (151), an electron transport auxiliarylayer, a buffer layer (141), etc., and the electron transport layer(160) and the like may serve as a hole blocking layer.

Although not shown, the organic electric element according to thepresent invention may further include a protective layer formed on atleast one side of the first and second electrodes, which is a sideopposite to the organic material layer.

Otherwise, even if the same core is used, the band gap, the electricalcharacteristics, the interface characteristics, and the like may varydepending on which substituent is bonded at which position, thereforethe choice of core and the combination of sub-substituents associatedtherewith is also very important, and in particular, when the optimalcombination of energy levels and T1 values and unique properties ofmaterials (mobility, interfacial characteristics, etc.) of each organicmaterial layer is achieved, a long life span and high efficiency can beachieved at the same time.

The organic electroluminescent device according to an embodiment of thepresent invention may be manufactured using a PVD (physical vapordeposition) method. For example, a metal or a metal oxide havingconductivity or an alloy thereof is deposited on a substrate to form acathode, and the organic material layer including the hole injectionlayer (130), the hole transport layer (140), the emitting layer (150),the electron transport layer (160), and the electron injection layer(170) is formed thereon, and then depositing a material usable as acathode thereon can manufacture an organic electroluminescent deviceaccording to an embodiment of the present invention.

In addition, an emission auxiliary layer (151) may be further formedbetween the hole transport layer (140) and the emitting layer (150), andan electron transport auxiliary layer may be further formed between theemitting layer (150) and the electron transport layer (160).

In addition, at least one hole transporting band layer is providedbetween the first electrode and the emitting layer, wherein the holetransporting band layer may include a hole transport layer, an emittingauxiliary layer or both, wherein the hole transporting band layerincludes an organic electronic element comprising the compoundrepresented by Formula (1).

The present invention may further include a light efficiency enhancinglayer formed on at least one of the opposite side to the organicmaterial layer among one side of the first electrode, or one of theopposite side to the organic material layer among one side of the secondelectrode.

Also, the present invention provides the organic electric elementwherein the organic material layer is formed by one of a spin coatingprocess, a nozzle printing process, an inkjet printing process, a slotcoating process, a dip coating process or a roll-to-roll process, andsince the organic material layer according to the present invention canbe formed by various methods, the scope of the present invention is notlimited by the method of forming the organic material layer.

As another specific example, the present invention provides an organicelectric element wherein the emitting layer in the organic materiallayer is a phosphorescent light emitting layer.

The compounds represented by Formula (1) and (2) are mixed in a ratio ofany one of 1:9 to 9:1 to be included in the emitting layer of theorganic material layer.

The compound represented by Formula (1) and (2) are mixed in a ratio ofany one of 1:9 to 5:5 to be included in the emitting. Preferably, themixing ratio of the compound represented by Formula (1) and the compoundrepresented by Formula (2) is mixed at a ratio of 1:9 or 5:5, to beincluded as the emitting layer, or the mixture ratio is mixed in a ratioof 2:8 to 3:7, to be used in the emitting layer. More preferably, themixing ratio of the compound represented by Formula (1) and the compoundrepresented by Formula (2) is mixed at a ratio of 2:8 or 3:7, to beincluded in the emitting layer.

In another aspect, in one embodiment of the present invention, thepresent invention provides a first electrode; a second electrode; and anorganic material layer disposed between the first electrode and thesecond electrode and including at least an hole transport layer, anemitting auxiliary layer and an emitting layer, wherein the holetransport layer or the emitting auxiliary layer comprise a compoundrepresented by Formula (1), wherein the emitting layer comprises acompound represented by Formula (2). That is, the compound representedby Formula (1) can be used as the material of the hole transport layerand/or the emitting auxiliary layer.

In another aspect, in one embodiment of the present invention, thepresent invention provides a first electrode; a second electrode; and anorganic material layer disposed between the first electrode and thesecond electrode and including at least an emitting auxiliary layer andan emitting layer, wherein at least one emitting auxiliary layermaterial of the organic material layers comprises a compound representedby Formula (1), wherein at least one host material in the emitting layercomprises a compound represented by Formula (2).

The organic electric element according to an embodiment of the presentinvention may be a front emission type, a back emission type, or aboth-sided emission type, depending on the material used.

WOLED (White Organic Light Emitting Device) has advantages of highresolution realization and excellent fairness, and can be manufacturedusing conventional LCD color filter technology. Various structures for awhite organic light emitting device mainly used as a backlight devicehave been proposed and patented. Representatively, there areside-by-side arrangement of the radiation part of the R (red), G (green)and B (blue), a stacking method in which R, G, and B emitting layers arelaminated on top and bottom, electroluminescence by the blue (B) organicemitting layer and, by using the light from this, a color conversionmaterial (CCM) method using a photo-luminescence of an inorganicphosphor, etc., and the present invention may be applied to such WOLED.

The present invention also provides an electronic device comprising adisplay device including the organic electric element; and a controlunit for driving the display device.

According to another aspect, the present invention provides an displaydevice wherein the organic electric element is at least one of an OLED,an organic solar cell, an organic photo conductor, an organic transistor(organic TFT) and an element for monochromic or white illumination.Here, the electronic device may be a wired/wireless communicationterminal which is currently used or will be used in the future, andcovers all kinds of electronic devices including a mobile communicationterminal such as a cellular phone, a personal digital assistant (PDA),an electronic dictionary, a point-to-multipoint (PMP), a remotecontroller, a navigation unit, a game player, various kinds of TVs, andvarious kinds of computers.

Hereinafter, Synthesis Examples of the compound represented by Formula(1) and (2) of the present invention and preparation examples of theorganic electric element of the present invention will be described indetail by way of example, but are not limited to the following examples.

Synthesis Example 1

I. Synthesis of Formula (1)

The final products 1 represented by Formula (1) of the present inventioncan be synthesized by reaction between Sub 1 and Sub 2 as illustrated inthe following Reaction Scheme 1 or Reaction Scheme 2.

When L⁵ of the Final Products of Reaction Scheme 1 is

Final Products 1′ can be synthesized by the following reaction path, butnot limited thereto.

Ar¹, Ar², Ar³, Ar⁴, L¹, L², L³, L⁴, Y, R⁸, R⁹, f′ and g′ are the same asdefined above.

In the reaction scheme 1′, the synthesis method disclosed in KoreanPatent No. 10-1668448 filed by the present applicant was used in thecase of Final Products 1′. (See Reaction Scheme 1)

1. Synthesis Example of Sub 1

Sub 1 of reaction scheme 1 can be synthesized by the reaction path ofthe following reaction scheme 3, but is not limited thereto.

A is Ar¹, Ar³; B is Ar², Ar³; C is L¹, L³; D is L², L⁴;

The synthesis examples of specific compounds belonging to Sub 1 are asfollows.

(1) Synthesis of Sub 1-1

Aniline (40 g, 429.5 mmol) was dissolved in toluene (3000 ml) in a roundbottom flask, and bromobenzene (74.18 g, 472.5 mmol), Pd₂(dba)₃ (19.66g, 21.5 mmol), 50% P(t-Bu)₃ (20.9 ml, 43 mmol), NaOt-Bu (136.22 g,1417.4 mmol)

were added and stirred at 100° C. After the reaction was completed, thereaction mixture was extracted with CH₂Cl₂ and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallized toobtain 54.51 g of the product. (yield: 75%)(2) Synthesis of Sub 1-11

[1,1′-biphenyl]-4-amine (30 g, 177.3 mmol), 4-bromo-1,1′-biphenyl (45.46g, 195 mmol), Pd₂(dba)₃ (8.12 g, 8.9 mmol), 50% P(t-Bu)₃ (8.6 ml, 17.7mmol), NaOt-Bu (56.23 g, 585 mmol), toluene (1860 ml) were carried outin the same manner as in Sub 1-1 to give the product (45.01 g, 79%).

(3) Synthesis of Sub 1-22

aniline (12.12 g, 130.16 mmol), 4-bromo-N,N-diphenylaniline (42.2 g130.16 mmol), Pd₂(dba)₃ (3.58 g, 3.90 mmol), P(t-Bu)₃ (1.58 g, 7.81mmol), NaOt-Bu (37.52 g, 390.48 mmol), toluene (1367 ml) were carriedout in the same manner as in Sub 1-1 to give the product (34.16 g, 78%).

(4) Synthesis of Sub 1-40

naphthalen-2-amine (14.85 g, 103.72 mmol),2-bromo-9,9′-spirobi[fluorene] (41 g, 103.72 mmol), Pd₂(dba)₃ (2.85 g,3.11 mmol), P(t-Bu)₃ (1.26 g, 6.22 mmol), NaOt-Bu (29.90 g, 311.16mmol), toluene (1089 ml) were carried out in the same manner as in Sub1-1 to give the product (34.17 g, 72%).

(5) Synthesis of Sub 1-46

aniline (15 g, 161.1 mmol), 2-bromo-9-phenyl-9H-carbazole (57.08 g,177.2 mmol), Pd₂(dba)₃ (7.37 g, 8.1 mmol), 50% P(t-Bu)₃ (7.9 ml, 16.1mmol), NaOt-Bu (51.08 g, 531.5 mmol), toluene (1690 ml) were carried outin the same manner as in Sub 1-1 to give the product (36.63 g, 68%).

(6) Synthesis of Sub 1-57

[1,1′-biphenyl]-4-amine (22.51 g, 133 mmol),2-bromodibenzo[b,d]thiophene (35 g, 133 mmol), Pd₂(dba)₃ (3.65 g, 3.99mmol), P(t-Bu)₃ (3.65 g, 3.99 mmol), NaOt-Bu (38.35 g, 399.01 mmol),toluene (1397 ml) were carried out in the same manner as in Sub 1-1 togive the product (34.59 g, 74%).

(7) Synthesis of Sub 1-69

4-(dibenzo[b,d]furan-2-yl)aniline (24.46 g, 94.33 mmol),2-(4-bromophenyl)dibenzo[b,d]thiophene (32 g, 94.33 mmol), Pd₂(dba)₃(2.59 g, 2.83 mmol), P(t-Bu)₃ (1.15 g, 5.66 mmol), NaOt-Bu (27.19 g,282.98 mmol), toluene (990 ml) were carried out in the same manner as inSub 1-1 to give the product (34.18 g, 70%).(8) Synthesis of Sub 1-93

3,5-dimethylaniline (21.88 g, 180.57 mmol),4-bromo-1,1′-biphenyl-2′,3′,4′,5′,6′-d₅ (43 g, 180.57 mmol), Pd₂(dba)₃(4.96 g, 5.42 mmol), P(t-Bu)₃ (2.19 g, 10.83 mmol), NaOt-Bu (52.06 g,541.70 mmol), toluene (1896 ml) were carried out in the same manner asin Sub 1-1 to give the product (34.18 g, 68%).

Examples of Sub 1 are as follows, but are not limited thereto

TABLE 1 compound FD-MS compound FD-MS Sub 1-1 m/z = 169.09(C₁₂H₁₁N =169.22) Sub 1-2 m/z = 219.10(C₁₆H₁₃N = 219.28) Sub 1-3 m/z =245.12(C₁₈H₁₅N = 245.32) Sub 1-4 m/z = 269.12(C₂₀H₁₅N = 269.34) Sub 1-5m/z = 245.12(C₁₈H₁₅N = 245.32) Sub 1-6 m/z = 245.12(C₁₈H₁₅N = 245.32)Sub 1-7 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 1-8 m/z = 295.14(C₂₂H₁₇N =295.38) Sub 1-9 m/z = 295.14(C₂₂H₁₇N = 295.38) Sub 1-10 m/z =295.14(C₂₂H₁₇N = 295.38) Sub 1-11 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub1-12 m/z = 321.15(C₂₄H₁₉N = 321.41) Sub 1-13 m/z = 369.15(C₂₈H₁₉N =369.47) Sub 1-14 m/z = 395.17(C₃₀H₂₁N = 395.51) Sub 1-15 m/z =295.14(C₂₂H₁₇N = 295.38) Sub 1-16 m/z = 652.25(C₄₈H₃₂N₂O = 652.80) Sub1-17 m/z = 371.17(C₂₈H₂₁N = 371.48) Sub 1-18 m/z = 371.17(C₂₈H₂₁N =371.48) Sub 1-19 m/z = 421.18(C₃₂H₂₃N = 421.54) Sub 1-20 m/z =371.17(C₂₈H₂₁N = 371.48) Sub 1-21 m/z = 447.20(C₃₄H₂₅N = 447.58) Sub1-22 m/z = 336.16(C₂₄H₂₀N₂ = 336.43) Sub 1-23 m/z = 503.24(C₃₆H₂₉N₃ =503.64) Sub 1-24 m/z = 285.15(C₂₁H₁₉N = 285.38) Sub 1-25 m/z =335.17(C₂₅H₂₁N = 335.44) Sub 1-26 m/z = 335.17(C₂₅H₂₁N = 335.44) Sub1-27 m/z = 361.18(C₂₇H₂₃N = 361.48) Sub 1-28 m/z = 451.23(C₃₄H₂₉N =451.61) Sub 1-29 m/z = 401.21(C₃₀H₂₇N = 401.55) Sub 1-30 m/z =477.25(C₃₆H₃₁N = 477.65) Sub 1-31 m/z = 391.14(C₂₇H₂₁NS = 391.53) Sub1-32 m/z = 391.14(C₂₇H₂₁NS = 391.53) Sub 1-33 m/z = 375.16(C₂₇H₂₁NO =375.46) Sub 1-34 m/z = 375.16(C₂₇H₂₁NO = 375.46) Sub 1-35 m/z =459.20(C₃₅H₂₅N = 459.58) Sub 1-36 m/z = 423.20(C₃₂H₂₅N = 423.56) Sub1-37 m/z = 586.24(C₄₄H₃₀N₂ = 586.74) Sub 1-38 m/z = 485.21(C₃₇H₂₇N =485.63) Sub 1-39 m/z = 407.17(C₃₁H₂₁N = 407.52) Sub 1-40 m/z =457.18(C₃₅H₂₃N = 457.58) Sub 1-41 m/z = 563.17(C₄₁H₂₅NS = 563.72) Sub1-42 m/z = 626.27(C₄₇H₃₄N₂ = 626.80) Sub 1-43 m/z = 284.13(C₂₀H₁₆N₂ =284.36) Sub 1-44 m/z = 246.12(C₁₇H₁₄N₂ = 246.31) Sub 1-45 m/z =296.13(C₂₁H₁₆N₂ = 296.37) Sub 1-46 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub1-47 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub 1-48 m/z = 460.19(C₃₄H₂₄N₂ =460.58) Sub 1-49 m/z = 384.16(C₂₈H₂₀N₂ = 384.48) Sub 1-50 m/z =500.19(C₃₆H₂₄N₂O = 500.60) Sub 1-51 m/z = 490.15(C₃₄H₂₂N₂S = 490.62) Sub1-52 m/z = 225.06(C₁₄H₁₁NS = 225.31) Sub 1-53 m/z = 275.08(C₁₈H₁₃NS =275.37) Sub 1-54 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 1-55 m/z =325.09(C₂₂H₁₅NS = 325.43) Sub 1-56 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub1-57 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 1-58 m/z = 351.11(C₂₄H₁₇NS =351.47) Sub 1-59 m/z = 401.12(C₂₈H₁₉NS = 401.53) Sub 1-60 m/z =401.12(C₂₈H₁₉NS = 401.53) Sub 1-61 m/z = 427.14(C₃₀H₂₁NS = 427.57) Sub1-62 m/z = 381.06(C₂₄H₁₅NS₂ = 381.51) Sub 1-63 m/z = 381.06(C₂₄H₁₅NS₂ =381.51) Sub 1-64 m/z = 452.13(C₃₁H₂₀N₂S = 452.58) Sub 1-65 m/z =351.11(C₂₄H₁₇NS = 351.47) Sub 1-66 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub1-67 m/z = 465.12(C₃₂H₁₉NOS = 465.57) Sub 1-68 m/z = 365.09(C₂₄H₁₅NOS =365.45) Sub 1-69 m/z = 517.15(C₃₇H₂₃NOS = 517.65) Sub 1-70 m/z =594.21(C₄₂H₃₀N₂S = 594.78) Sub 1-71 m/z = 259.10(C₁₈H₁₃NO = 259.31) Sub1-72 m/z = 259.10(C₁₈H₁₃NO = 259.31) Sub 1-73 m/z = 259.10(C₁₈H₁₃NO =259.31) Sub 1-74 m/z = 309.12(C₂₂H₁₅NO = 309.36) Sub 1-75 m/z =335.13(C₂₄H₁₇NO = 335.40) Sub 1-76 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub1-77 m/z = 335.13(C₂₄H₁₇NO = 335.40) Sub 1-78 m/z = 335.13(C₂₄H₁₇NO =335.40) Sub 1-79 m/z = 485.18(C₃₆H₂₃NO = 485.59) Sub 1-80 m/z =349.11(C₂₄H₁₅NO₂ = 349.39) Sub 1-81 m/z = 411.16(C₃₀H₂₁NO = 411.49) Sub1-82 m/z = 225.15(C₁₆H₁₉N = 225.34) Sub 1-83 m/z = 275.17(C₂₀H₂₁N =275.40) Sub 1-84 m/z = 234.12(C₁₆H₁₄N²⁻ = 234.30) Sub 1-85 m/z =369.15(C₂₅H₂₀FNO = 369.44) Sub 1-86 m/z = 365.16(C₂₅H₂₃NSi = 365.55) Sub1-87 m/z = 382.38(C₂₂H₁₄N₄O₃ = 382.38) Sub 1-88 m/z = 376.10(C₂₅H₁₆N₂S =376.48) Sub 1-89 m/z = 322.15(C₂₃H₁₈N₂ = 322.41) Sub 1-90 m/z =224.14(C₁₆H₈D₅N = 224.32) Sub 1-91 m/z = 250.15(C₁₈H₁₀D₅N = 250.36) Sub1-92 m/z = 250.15(C₁₈H₁₀D₅N = 250.36) Sub 1-93 m/z = 278.18(C₂₀H₁₄D₅N =278.41) Sub 1-94 m/z = 386.18(C₂₈H₂₂N₂ = 386.50) Sub 1-95 m/z =512.23(C₃₈H₂₈N₂ = 512.66) Sub 1-96 m/z = 295.14(C₂₂H₁₇N = 295.39) Sub1-97 m/z = 269.12(C₂₀H₁₅N = 269.35) Sub 1-98 m/z = 321.15(C₂₄H₁₉N =321.42) Sub 1-99 m/z = 346.15(C₂₅H₁₈N₂ = 346.43) Sub 1-100 m/z =275.08(C₁₈H₁₃NS = 275.37) Sub 1-101 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub1-102 m/z = 290.09(C₁₈H₁₄N₂S = 290.38) Sub 1-103 m/z = 309.12(C₂₂H₁₅NO =309.37) Sub 1-104 m/z = 334.15(C₂₄H₁₈N₂ = 334.42) Sub 1-105 m/z =410.18(C₃₀H₂₂N₂ = 410.52) Sub 1-106 m/z = 450.21(C₃₃H₂₆N₂ = 450.59) Sub1-107 m/z = 460.19(C₃₄H₂₄N₂ = 460.58) Sub 1-108 m/z = 434.18(C₃₂H₂₂N₂ =434.54) Sub 1-109 m/z = 247.11(C₁₆H₁₃N₃ = 247.30) Sub 1-110 m/z =217.09(C₁₃H₁₂FNO = 217.24) Sub 1-111 m/z = 300.17(C₂₂H₁₂D₅N = 300.42)Sub 1-112 m/z = 276.16(C₂₀H₈D₇N = 276.39) Sub 1-113 m/z =298.19(C₁₉H₁₄D₇NSi = 298.51)2. Synthesis of Sub 2

Sub 2 of Reaction Scheme 1 can be synthesized by the reaction path ofthe following Reaction Scheme 4 or 5, but is not limited thereto.

Examples of synthesis of specific compounds belonging to Sub 2 and Sub2A are as follows.

Synthesis of Sub 2A-1

1) Synthesis of Intermediate Sub 2A-I-1

phenyl boronic acid (66.4 g, 544.5 mmol) was dissolved in THF (2396 mL)in a round bottom flask, and 1-bromo-2-nitrobenzene (110 g, 544.5 mmol),Pd(PPh₃)₄ (18.9 g, 16.3 mmol), K₂CO₃ (225.8 g, 1633.6 mmol), and water(1198 ml) were added and refluxed with stirring. After the reaction wascompleted, the reaction mixture was extracted with ether and water. Theorganic layer was dried over MgSO₄ and concentrated. The resultingorganic material was separated by silicagel column chromatography andrecrystallization to obtain 99.8 g (yield: 92%) of the product.

2) Synthesis of Intermediate Sub 2A-II-1

Sub 2A-I-1 (95 g, 476.9 mmol), Triphenylphosphine (375.2 g, 1430.7mmol), o-Dichlorobenzene (1907.5 ml) were added in a round bottom flaskand refluxed at 180° C. After the reaction was completed, the reactionmixture was cooled to room temperature and extracted withmethylenechloride and water. The organic layer was dried over MgSO₄ andconcentrated. The resulting organic material was separated by silicagelcolumn chromatography and recrystallization to obtain 67 g (yield: 84%)of the product.

3) Synthesis of Sub 2A-1

Sub 2A-II-1 (59 g, 352.9 mmol) was dissolved in nitrobenzene (1765 ml)in a round bottom flask, and 4-bromo-4′-iodo-1,1′-biphenyl (139.3 g,388.1 mmol), Na₂SO₄ (50.1 g, 352.9 mmol), K₂CO₃ (48.8 g, 352.9 mmol), Cu(6.7 g, 105.9 mmol) were added and stirred at 200° C. When the reactionwas complete, nitrobenzene was removed by distillation and extractedwith CH₂Cl₂ and water. The organic layer was dried over MgSO₄ andconcentrated. The resulting compound was separated by silicagel columnchromatography and recrystallization to obtain 102.6 g (yield: 73%) ofthe product.

Synthesis of Sub 2A-9

1) Synthesis of Intermediate Sub 2A-I-2

phenylboronic acid (65.8 g, 539.4 mmol), THF (2373 ml),3-bromo-4-nitro-1,1′-biphenyl (150 g, 539.4 mmol), Pd(PPh₃)₄ (18.7 g,16.2 mmol), K₂CO₃ (223.6 g, 1618 mmol) and water (1187 ml) were carriedout in the same manner as Sub 2A-I-1 to obtain 106.9 g of the product(yield: 72%)

2) Synthesis of Intermediate Sub 2A-II-2

Sub 2A-I-2 (100 g, 363.2 mmol), Triphenylphosphine (285.8 g, 1089.7mmol), o-Dichlorobenzene (1453 mL) were carried out in the same manneras Sub 2A-II-1 to obtain 54.8 g of the product (yield: 62%)

3) Synthesis of Sub 2A-9

Sub 2A-II-2 (40 g, 164.4 mmol), nitrobenzene (822 ml),4-bromo-4′-iodo-1,1′-biphenyl (64.9 g, 180.8 mmol), Na₂SO₄ (23.4 g,164.4 mmol), K₂CO₃ (22.7 g, 164.4 mmol), Cu (3.1 g, 49.3 mmol) werecarried out in the same manner as Sub 2A-1 to obtain 55.4 g of theproduct (yield: 71%)

Synthesis of Sub 2A-18

Sub 2A-II-1 (30 g, 179.4 mmol), nitrobenzene (897 ml),5-bromo-9-iododinaphtho[2,1-b:1′,2′-d]thiophene (96.5 g, 197.4 mmol),Na₂SO₄ (25.5 g, 179.4 mol), K₂CO₃ (24.8 g, 179.4 mmol), Cu (3.4 g, 53.8mmol) were carried out in the same manner as Sub 2A-1 to obtain 61.6 gof the product (yield: 65%)

Synthesis of Sub 2A-20

Sub 2A-II-1 (30 g, 179.4 mmol), nitrobenzene (897 ml),2-bromo-7-iodo-9,9-diphenyl-9H-fluorene (78.8 g, 197.4 mmol), Na₂SO₄(25.5 g, 179.4 mmol), K₂CO₃ (24.8 g, 179.4 mmol), Cu (3.4 g, 53.8 mmol)were carried out in the same manner as Sub 2A-1 to obtain 53 g of theproduct (yield: 69%)

Synthesis of Sub 2A-19

Sub 2A-II-1 (30 g, 179.4 mmol), nitrobenzene (897 ml),2-bromo-7-iodo-9,9-diphenyl-9H-fluorene (78.8 g, 197.4 mmol), Na₂SO₄(25.5 g, 179.4 mmol), K₂CO₃ (24.8 g, 179.4 mmol), Cu (3.4 g, 53.8 mmol)were carried out in the same manner as Sub 2A-1 to obtain 49.6 g of theproduct (yield: 67%)

Synthesis of Sub 2A-22

Sub 2A-II-1 (30 g, 179.4 mmol), nitrobenzene (897 ml),2-bromo-7-iodo-9,9-dimethyl-9H-fluorene (78.8 g, 197.4 mmol), Na₂SO₄(25.5 g, 179.4 mmol), K₂CO₃ (24.8 g, 179.4 mmol), Cu (3.4 g, 53.8 mmol)were carried out in the same manner as Sub 2A-1 to obtain 52.7 g of theproduct (yield: 67%)

Synthesis of Sub 2A-33

1) Synthesis of Intermediate Sub 2A-I-3

naphthalen-1-ylboronic acid (68.2 g, 396.7 mmol), THF (1745 ml),2-bromo-1-nitronaphthalene (100 g, 396.7 mmol), Pd(PPh₃)₄ (13.8 g, 11.9mmol), K₂CO₃ (164.5 g, 1190 mmol) and water (873 ml) were carried out inthe same manner as Sub 2A-I-1 to obtain 83.1 g of the product (yield:70%)

2) Synthesis of Intermediate Sub 2A-II-3

Sub 2A-I-3 (80 g, 267.3 mmol), Triphenylphosphine (210.3 g, 801.8 mmol),o-Dichlorobenzene (1069 mL) were carried out in the same manner as Sub2A-II-1 to obtain 45.7 g of the product (yield: 64%)

3) Synthesis of Sub 2A-33

Sub 2A-II-3 (45 g, 168.3 mmol), nitrobenzene (842 ml),4′-bromo-3-iodo-1,1′-biphenyl (66.5 g, 185.2 m mol), Na₂SO₄ (23.9 g,168.3 mmol), K₂CO₃ (23.3 g, 168.3 mmol), Cu (3.2 g, 50.5 mmol) werecarried out in the same manner as Sub 2A-1 to obtain 50.3 g of theproduct (yield: 60%)

Synthesis of Sub 2A-34

1) Synthesis of Intermediate Sub 2A-I-4

naphthalen-1-ylboronic acid (44.05 g, 198.36 mmol), THF (873 ml),2-bromo-1-nitronaphthalene (50 g, 198.36 mmol), Pd(PPh₃)₄ (6.88 g, 5.95mmol), K₂CO₃ (82.25 g, 595.07 mmol) and water (436 ml) were carried outin the same manner as Sub 2A-I-1 to obtain 57.52 g of the product(yield: 83%)

2) Synthesis of Intermediate Sub 2A-II-4

Sub 2A-I-4 (57.52 g, 164.63 mmol), Triphenylphosphine (107.95 g, 411.57mmol), o-Dichlorobenzene (823 ml) were carried out in the same manner asSub 2A-II-1 to obtain 22.99 g of the product (yield: 44%)

3) Synthesis of Sub 2A-34

Sub 2A-II-4 (22.99 g, 72.44 mmol), nitrobenzene (362 ml),4′-bromo-3-iodo-1,1′-biphenyl (22.67 g, 72.44 mmol), Na₂SO₄ (5.14 g,36.22 mmol), K₂CO₃ (5.01 g, 36.22 mmol), Cu (0.69 g, 10.87 mmol) werecarried out in the same manner as Sub 2A-1 to obtain 26.27 g of theproduct (yield: 66%)

Synthesis of Sub 2-1

Sub 1-2 (20.16 g, 91.92 mmol) was dissolved in toluene (965 ml) in around bottom flask, and 4-bromo-4′-iodo-1,1′-biphenyl (33 g, 91.92mmol), Pd₂(dba)₃ (1.26 g, 1.38 mmol), P(t-Bu)₃ (0.56 g, 2.76 mmol),NaOt-Bu (13.25 g, 137.88 mmol) were added and stirred at 70° C. When thereaction was complete, the reaction mixture was extracted with CH₂Cl₂and water. The organic layer was dried over MgSO₄ and concentrated. Theresulting compound was separated by silicagel column chromatography andrecrystallization to obtain 28.15 g (yield: 68%) of the product.

Synthesis of Sub 2-7

Sub 1-92 (17.43 g, 69.64 mmol), toluene (731 ml),3-bromo-3′-iodo-1,1′-biphenyl (25 g, 69.64 mmol), Pd₂(dba)₃ (0.96 g,1.04 mmol), P(t-Bu)₃ (0.42 g, 2.09 mmol), NaOt-Bu (10.04 g, 104.46 mmol)were carried out in the same manner as Sub 2-1 to obtain 23.13 g of theproduct (yield: 69%)

Synthesis of Sub 2-14

Sub 1-65 (24.48 g, 69.64 mmol), toluene (731 ml),2-bromo-6-iodonaphthalene (25 g, 69.64 mmol), Pd₂(dba)₃ (0.96 g, 1.04mmol), P(t-Bu)₃ (0.42 g, 2.09 mmol), NaOt-Bu (10.04 g, 104.46 mmol) werecarried out in the same manner as Sub 2-1 to obtain 27.18 g of theproduct (yield: 67%)

Synthesis of Sub 2-28

Sub 1-2 (21.87 g, 66.99 mmol), toluene (703 ml), 3,3″-dibromo-1,1′:3′,1″-terphenyl (26 g, 66.99 mmol), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃(0.41 g, 2.01 mmol), NaOt-Bu (9.66 g, 100.49 mmol) were carried out inthe same manner as Sub 2-1 to obtain 21.87 g of the product (yield: 62%)

Synthesis of Sub 2-29

Sub 1-74 (20.73 g, 66.99 mmol), toluene (703 ml), 3,3″-dibromo-1,1′:2′,1″-terphenyl (26 g, 66.99 mmol), Pd₂(dba)₃ (0.92 g, 1 mmol), P(t-Bu)₃(0.41 g, 2.01 mmol), NaOt-Bu (9.66 g, 100.49 mmol) were carried out inthe same manner as Sub 2-1 to obtain 24.78 g of the product (yield: 60%)

Synthesis of Sub 2-36

Sub 1-106 (31.12 g, 69.08 mmol), toluene (725 ml),2-bromo-6-iodonaphthalene (23 g, 69.08 mmol), Pd₂(dba)₃ (0.95 g, 1.04mmol), P(t-Bu)₃ (0.42 g, 2.07 mmol), NaOt-Bu (9.96 g, 103.61 mmol) werecarried out in the same manner as Sub 2-1 to obtain 28.98 g of theproduct (yield: 64%)

Synthesis of Sub 2-44

Sub 1-55 (25.96 g, 79.76 mmol), toluene (837 ml),3,7-dibromodibenzo[b,d]furan (26 g, 79.76 mmol), Pd₂(dba)₃ (1.10 g, 1.20mmol), P(t-Bu)₃ (0.48 g, 2.39 mmol), NaOt-Bu (11.5 g, 119.64 mmol) werecarried out in the same manner as Sub 2-1 to obtain 30.94 g of theproduct (yield: 68%)

Synthesis of Sub 2-56

Sub 1-25 (20.37 g, 60.72 mmol), toluene (638 ml),2-bromo-7-(4-bromophenyl)-9,9-dimethyl-9H-fluorene (26 g, 60.72 mmol),Pd₂(dba)₃ (0.83 g, 0.91 mmol), P(t-Bu)₃ (0.37 g, 1.82 mmol), NaOt-Bu(8.75 g, 91.09 mmol) were carried out in the same manner as Sub 2-1 toobtain 25.70 g of the product (yield: 62%)

Synthesis of Sub 2-59

Sub 1-6 (14.90 g, 60.72 mmol), toluene (638 ml),2-(3,5-dibromophenyl)-9,9-dimethyl-9H-fluorene (26 g, 60.72 mmol),Pd₂(dba)₃ (0.83 g, 0.91 mmol), P(t-Bu)₃ (0.37 g, 1.82 mmol), NaOt-Bu(8.75 g, 91.09 mmol) were carried out in the same manner as Sub 2-1 toobtain 21.23 g of the product (yield: 59%)

Examples of Sub 2 and Sub 2A are as follows, but are not limitedthereto.

TABLE 2 compound FD-MS compound FD-MS Sub 2A-1 m/z = 397.05(C₂₄H₁₆BrN =398.29) Sub 2A-2 m/z = 474.07(C₂₉H₁₉BrN₂ = 475.38) Sub 2A-3 m/z =397.05(C₂₄H₁₆BrN = 398.29) Sub 2A-4 m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub2A-5 m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub 2A-6 m/z = 397.05(C₂₄H₁₆BrN =398.29) Sub 2A-7 m/z = 397.05(C₂₄H₁₆BrN = 398.29) Sub 2A-8 m/z =474.96(C₂₄H₁₅Br₂N = 477.20) Sub 2A-9 m/z = 473.08(C₃₀H₂₀BrN = 474.39)Sub 2A-10 m/z = 478.11(C₃₀H₁₅D₅BrN = 479.43) Sub 2A-11 m/z =550.10(C₃₅H₂₃BrN₂ = 551.49) Sub 2A-12 m/z = 579.07(C₃₆H₂₂BrNS = 580.54)Sub 2A-13 m/z = 638.14(C₄₂H₂₇BrN₂ = 639.58) Sub 2A-14 m/z =321.02(C₁₈H₁₂BrN = 322.20) Sub 2A-15 m/z = 447.06(C₂₈H₁₈BrN = 448.35)Sub 2A-16 m/z = 473.08(C₃₀H₂₀BrN = 474.40) Sub 2A-17 m/z =493.14(C₃₁H₂₈BrN = 494.48) Sub 2A-18 m/z = 527.03(C₃₂H₁₈BrNS = 528.46)Sub 2A-19 m/z = 411.03(C₂₄H₁₄BrNO = 412.28) Sub 2A-20 m/z =427.00(C₂₄H₁₄BrNS = 428.34) Sub 2A-21 m/z = 411.03(C₂₄H₁₄BrNO = 412.28)Sub 2A-22 m/z = 437.08(C₂₇H₂₀BrN = 438.36) Sub 2A-23 m/z =561.11(C₃₇H₂₄BrN = 562.50) Sub 2A-24 m/z = 487.09(C₃₁H₂₂BrN = 488.42)Sub 2A-25 m/z = 561.11(C₃₇H₂₄BrN = 562.50) Sub 2A-26 m/z =611.12(C₄₁H₂₆BrN = 612.56) Sub 2A-27 m/z = 559.09(C₃₇H₂₂BrN = 560.48)Sub 2A-28 m/z = 447.06(C₂₈H₁₈BrN = 448.35) Sub 2A-29 m/z =447.06(C₂₈H₁₈BrN = 448.35) Sub 2A-30 m/z = 447.06(C₂₈H₁₈BrN = 448.35)Sub 2A-31 m/z = 497.08(C₃₂H₂₀BrN = 498.41) Sub 2A-32 m/z =497.08(C₃₂H₂₀BrN = 498.41) Sub 2A-33 m/z = 497.08(C₃₂H₂₀BrN = 498.41)Sub 2A-34 m/z = 548.09(C₃₅H₂₁BrN₂ = 549.46) Sub 2A-35 m/z =597.11(C₄₀H₂₄BrN = 598.53) Sub 2A-36 m/z = 497.08(C₃₂H₂₀BrN = 498.41)Sub 2-1 m/z = 449.08(C₂₈H₂₀BrN = 450.37) Sub 2-2 m/z = 525.11(C₃₄H₂₄BrN= 526.48) Sub 2-3 m/z = 551.12(C₃₆H₂₆BrN = 552.50) Sub 2-4 m/z =499.09(C₃₂H₂₂BrN = 500.43) Sub 2-5 m/z = 530.14(C₃₄H₁₉D₅BrN = 531.51)Sub 2-6 m/z = 506.14(C₃₂H₁₅D₇BrN = 507.48) Sub 2-7 m/z =480.12(C₃₀H₁₇D₅BrN = 481.45) Sub 2-8 m/z = 565.14(C₃₇H₂₈BrN = 566.54)Sub 2-9 m/z = 631.19(C₄₂H₃₄BrN = 632.65) Sub 2-10 m/z =576.12(C₃₇H₂₅BrN₂ = 577.53) Sub 2-11 m/z = 555.07(C₃₄H₂₂BrNS = 556.51)Sub 2-12 m/z = 581.08(C₃₆H₂₄BrNS = 582.55) Sub 2-13 m/z =611.04(C₃₆H₂₂BrNS₂ = 612.60) Sub 2-14 m/z = 581.08(C₃₆H₂₄BrNS = 582.55)Sub 2-15 m/z = 704.28(C₅₂H₃₆N₂O = 704.87) Sub 2-16 m/z =520.06(C₃₀H₂₁BrN₂S = 521.48) Sub 2-17 m/z = 539.09(C₃₄H₂₂BrNO = 540.45)Sub 2-18 m/z = 564.12(C₃₆H₂₅BrN₂ = 565.50) Sub 2-19 m/z =690.17(C₄₆H₃₁BrN₂ = 691.67) Sub 2-20 m/z = 657.11(C₄₂H₂₈BrNS = 658.65)Sub 2-21 m/z = 564.12(C₃₆H₂₅BrN₂ = 565.50) Sub 2-22 m/z =664.15(C₄₄H₂₉BrN₂ = 665.63) Sub 2-23 m/z = 525.11(C₃₄H₂₄BrN = 526.47)Sub 2-24 m/z = 601.14(C₄₀H₂₈BrN = 602.58) Sub 2-25 m/z =551.12(C₃₆H₂₆BrN = 552.52) Sub 2-26 m/z = 525.11(C₃₄H₂₄BrN = 526.47) Sub2-27 m/z = 525.11(C₃₄H₂₄BrN = 526.47) Sub 2-28 m/z = 525.11(C₃₄H₂₄BrN =526.47) Sub 2-29 m/z = 581.08(C₃₆H₂₄BrNS = 582.55) Sub 2-30 m/z =615.12(C₄₀H₂₆BrNO = 616.54) Sub 2-31 m/z = 641.14(C₄₂H₂₈BrNO = 642.58)Sub 2-32 m/z = 716.18(C₄₈H₃₃BrN₂ = 717.71) Sub 2-33 m/z =475.09(C₃₀H₂₂BrN = 476.41) Sub 2-34 m/z = 625.14(C₄₂H₂₈BrN = 626.58) Sub2-35 m/z = 503.12(C₃₂H₂₆BrN = 504.46) Sub 2-36 m/z = 538.10(C₃₄H₂₃BrN₂ =539.46) Sub 2-37 m/z = 449.08(C₂₈H₂₀BrN = 450.38) Sub 2-38 m/z =499.09(C₃₂H₂₂BrN = 500.43) Sub 2-39 m/z = 499.09(C₃₂H₂₂BrN = 500.43) Sub2-40 m/z = 549.11(C₃₆H₂₄BrN = 550.50) Sub 2-41 m/z = 651.16(C₄₄H₃₀BrN =652.64) Sub 2-42 m/z = 538.10(C₃₄H₂₃BrN₂ = 539.46) Sub 2-43 m/z =538.10(C₃₄H₂₃BrN₂ = 539.46) Sub 2-44 m/z = 569.04(C₃₄H₂₀BrNOS = 570.50)Sub 2-45 m/z = 479.03(C₂₈H₁₈BrNS = 480.42) Sub 2-46 m/z =544.06(C₃₂H₂₁BrN₂S = 545.49) Sub 2-47 m/z = 605.08(C₃₈H₂₄BrNS = 606.57)Sub 2-48 m/z = 579.12(C₃₇H₂₆BrNO = 580.53) Sub 2-49 m/z =515.12(C₃₃H₂₆BrN = 516.48) Sub 2-50 m/z = 505.05(C₃₀H₂₀BrNS = 506.46)Sub 2-51 m/z = 559.06(C₃₆H₂₂BrNOS = 596.54) Sub 2-52 m/z =519.03(C₃₀H₁₈BrNOS = 520.44) Sub 2-53 m/z = 595.10(C₃₇H₂₆BrNS = 596.59)Sub 2-54 m/z = 612.12(C₃₉H₂₅BrN₂O = 617.55) Sub 2-55 m/z =640.15(C₄₂H₂₉BrN₂ = 641.61) Sub 2-56 m/z = 681.20(C₄₆H₃₆BrN = 682.71)Sub 2-57 m/z = 489.07(C₃₀H₂₀BrNO = 490.40) Sub 2-58 m/z =627.16(C₄₂H₃₀BrN = 628.61) Sub 2-59 m/z = 591.16(C₃₉H₃₀BrN = 592.58) Sub2-60 m/z = 555.07(C₃₄H₂₂BrNS = 556.52) Sub 2-61 m/z = 611.04(C₃₆H₂₂BrNS₂= 612.60) Sub 2-62 m/z = 616.15(C₄₀H₂₉BrN₂ = 617.59) Sub 2-63 m/z =477.08(C₂₈H₂₀BrN₃ = 478.39) Sub 2-64 m/z = 447.06(C₂₅H₁₉BrFNO = 448.34)Sub 2-65 m/z = 528.16(C₃₁H₂D₅BrNSi = 529.60)Synthesis Example of Final Products 1

Sub 2 or Sub 2A (1 eq.) was dissolved in toluene in a round bottomflask, and Sub 1 (1.1 eq.), Pd₂(dba)₃ (0.03 eq.), P(t-Bu)₃ (0.1 eq.),NaOt-Bu (3 eq.) were added and stirred at 100° C. When the reaction wascomplete, the reaction mixture was extracted with CH₂Cl₂ and water. Theorganic layer was dried over MgSO₄ and concentrated. The resultingcompound was separated by silicagel column chromatography andrecrystallization to obtain the Final products.

Synthesis of 1-3

Sub 2A-1 (10 g, 25.11 mmol) was dissolved in toluene (264 ml) in a roundbottom flask, and Sub 1-11 (8.88 g, 27.62 mmol), Pd₂(dba)₃ (0.69 g, 0.75mmol), P(t-Bu)₃ (0.51 g, 2.51 mmol), NaOt-Bu (7.24 g, 75.32 mmol) wereadded and stirred at 100° C. When the reaction was complete, thereaction mixture was extracted with CH₂Cl₂ and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain 13.31 g of product. (yield: 83%)

Synthesis of 1-23

Sub 2A-3 (10 g, 25.11 mmol), toluene (264 ml), Sub 1-76 (9.26 g, 27.62mmol), Pd₂(dba)₃ (0.69 g, 0.75 mmol), P(t-Bu)₃ (0.51 g, 2.51 mmol),NaOt-Bu (7.24 g, 75.32 mmol) were carried out in the same manner as 1-3to obtain 12.78 g of the product (yield: 78%)

Synthesis of 1-31

1) Synthesis of Intermediate 1-I-31

Sub 2A-8 (20 g, 41.91 mmol), toluene (440 ml), Sub 1-57 (16.20 g, 46.10mmol), Pd₂(dba)₃ (0.58 g, 0.63 mmol), P(t-Bu)₃ (0.42 g, 2.10 mmol),NaOt-Bu (6.04 g, 62.87 mmol) were carried out in the same manner as 1-3to obtain 22.25 g of the product (yield: 71%)

2) Synthesis of 1-31

1-I-31 (22.25 g, 29.76 mmol), toluene (312 ml), Sub 1-1 (5.54 g, 32.73mmol), Pd₂(dba)₃ (0.82 g, 0.89 mmol), P(t-Bu)₃ (0.60 g, 2.98 mmol),NaOt-Bu (8.58 g, 89.27 mmol) were carried out in the same manner as 1-3to obtain 20.65 g of the product (yield: 83%)

Synthesis of 1-34

Sub 2A-13 (11 g, 17.20 mmol), toluene (181 ml), Sub 1-6 (4.64 g, 18.92mmol), Pd₂(dba)₃ (0.47 g, 0.52 mmol), P(t-Bu)₃ (0.35 g, 1.72 mmol),NaOt-Bu (4.96 g, 51.59 mmol) were carried out in the same manner as 1-3to obtain 10.65 g of the product (yield: 77%)

Synthesis of 1-43

Sub 2A-20 (11 g, 25.68 mmol), toluene (270 ml), Sub 1-49 (10.86 g, 28.25mmol), Pd₂(dba)₃ (0.71 g, 0.77 mmol), P(t-Bu)₃ (0.52 g, 2.57 mmol),NaOt-Bu (7.40 g, 77.04 mmol) were carried out in the same manner as 1-3to obtain 13.16 g of the product (yield: 70%)

Synthesis of 1-45

Sub 2A-22 (11 g, 25.09 mmol), toluene (263 ml), Sub 1-89 (8.90 g, 27.60mmol), Pd₂(dba)₃ (0.69 g, 0.75 mmol), P(t-Bu)₃ (0.51 g, 2.51 mmol),NaOt-Bu (7.23 g, 75.28 mmol) were carried out in the same manner as 1-3to obtain 11.43 g of the product (yield: 67%)

Synthesis of 1-54

Sub 2A-30 (7 g, 15.61 mmol), toluene (164 ml), Sub 1-69 (8.89 g, 17.17mmol), Pd₂(dba)₃ (0.43 g, 0.47 mmol), P(t-Bu)₃ (0.32 g, 1.56 mmol),NaOt-Bu (4.50 g, 46.84 mmol) were carried out in the same manner as 1-3to obtain 10.23 g of the product (yield: 74%)

Synthesis of 1-56

Sub 2A-32 (9 g, 18.06 mmol), toluene (190 ml), Sub 1-33 (7.46 g, 19.86mmol), Pd₂(dba)₃ (0.50 g, 0.54 mmol), P(t-Bu)₃ (0.37 g, 1.81 mmol),NaOt-Bu (5.21 g, 54.17 mmol) were carried out in the same manner as 1-3to obtain 10.17 g of the product (yield: 71%)

Synthesis of 2-1

Sub 2-1 (10 g, 22.20 mmol) was dissolved in toluene (233 ml) in a roundbottom flask, and Sub 1-12 (5.36 g, 24.42 mmol), Pd₂(dba)₃ (0.61 g, 0.67mmol), P(t-Bu)₃ (0.45 g, 2.22 mmol), NaOt-Bu (6.40 g, 66.61 mmol) wereadded and stirred at 100° C. When the reaction was complete, thereaction mixture was extracted with CH₂Cl₂ and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain 10.46 g of product. (yield: 80%)

Synthesis of 2-10

Sub 2-1 (8 g, 17.76 mmol), toluene (187 ml), Sub 1-35 (8.98 g, 19.54mmol), Pd₂(dba)₃ (0.49 g, 0.53 mmol), P(t-Bu)₃ (0.36 g, 1.78 mmol),NaOt-Bu (5.12 g, 53.29 mmol) were carried out in the same manner as 2-1to obtain 10.6 g of the product (yield: 72%)

Synthesis of 2-23

Sub 2-20 (9 g, 15.91 mmol), toluene (167 ml), Sub 1-47 (5.85 g, 17.51mmol), Pd₂(dba)₃ (0.44 g, 0.48 mmol), P(t-Bu)₃ (0.32 g, 1.59 mmol),NaOt-Bu (4.59 g, 47.74 mmol) were carried out in the same manner as 2-1to obtain 10.04 g of the product (yield: 77%)

Synthesis of 2-25

Sub 2-7 (10 g, 20.77 mmol), toluene (218 ml), Sub 1-92 (5.72 g, 22.85mmol), Pd₂(dba)₃ (0.57 g, 0.62 mmol), P(t-Bu)₃ (0.42 g, 2.08 mmol),NaOt-Bu (5.99 g, 62.31 mmol) were carried out in the same manner as 2-1to obtain 10.68 g of the product (yield: 79%)

Synthesis of 2-27

Sub 2-29 (11 g, 18.88 mmol), toluene (198 ml), Sub 1-73 (5.39 g, 20.77mmol), Pd₂(dba)₃ (0.52 g, 0.57 mmol), P(t-Bu)₃ (0.38 g, 1.89 mmol),NaOt-Bu (5.44 g, 56.65 mmol) were carried out in the same manner as 2-1to obtain 10.49 g of the product (yield: 73%)

Synthesis of 2-41

Sub 2-36 (11 g, 16.78 mmol), toluene (176 ml), Sub 1-46 (6.17 g, 18.46mmol), Pd₂(dba)₃ (0.46 g, 0.50 mmol), P(t-Bu)₃ (0.34 g, 1.68 mmol),NaOt-Bu (4.84 g, 50.33 mmol) were carried out in the same manner as 2-1to obtain 10.22 g of the product (yield: 67%)

Synthesis of 2-50

Sub 2-45 (9.5 g, 19.77 mmol), toluene (208 ml), Sub 1-11 (6.99 g, 21.75mmol), Pd₂(dba)₃ (0.54 g, 0.59 mmol), P(t-Bu)₃ (0.40 g, 1.98 mmol),NaOt-Bu (5.70 g, 59.32 mmol) were carried out in the same manner as 2-1to obtain 10.41 g of the product (yield: 73%)

Meanwhile, FD-MS values of the compounds 1-1 to 1-60 and 2-1 to 2-70 ofthe present invention prepared according to the above synthesis examplesare shown in Table 3 below.

TABLE 3 compound FD-MS compound FD-MS 1-1 m/z = 473.21(C₃₆H₂₇N = 473.61)1-2 m/z = 523.23(C₄₀H₂₉N = 523.66) 1-3 m/z = 573.25(C₄₄H₃₁N = 573.72)1-4 m/z = 623.26(C₄₈H₃₃N = 623.78) 1-5 m/z = 738.30(C₅₆H₃₈N₂ = 738.91)1-6 m/z = 688.29(C₅₂H₃₆N₂ = 688.87) 1-7 m/z = 653.28(C₄₈H₃₅N₃ = 653.81)1-8 m/z = 820.36(C₆₀H₄₄N₄ = 821.02) 1-9 m/z = 727.30(C₅₄H₃₇N₃ = 727.89)1-10 m/z = 668.23(C₄₈H₃₂N₂S = 668.85) 1-11 m/z = 802.30(C₆₀H₃₈N₂O =802.98) 1-12 m/z = 698.19(C₄₈H₃₀N₂S = 698.90) 1-13 m/z =911.33(C₆₆H₄₅N₃S = 912.17) 1-14 m/z = 759.23(C₅₃H₃₃N₃OS = 759.93) 1-15m/z = 652.29(C₄₉H₃₆N₂ = 652.84) 1-16 m/z = 692.28(C₅₁H₃₆N₂O = 692.84)1-17 m/z = 794.37(C₆₀H₄₆N₂ = 795.02) 1-18 m/z = 903.36(C₆₈H₄₅N₃ =904.10) 1-19 m/z = 638.27(C₄₈H₃₄N₂ = 638.80) 1-20 m/z = 880.29(C₆₅H₄₀N₂S= 881.11) 1-21 m/z = 777.31(C₅₈H₃₉N₃ = 777.97) 1-22 m/z =718.24(C₅₂H₃₄N₂S = 718.92) 1-23 m/z = 652.25(C₄₈H₃₂N₂O = 652.78) 1-24m/z = 688.29(C₅₂H₃₆N₂ = 688.87) 1-25 m/z = 668.23(C₄₈H₃₂N₂S = 668.85)1-26 m/z = 698.19(C₄₈H₃₀N₂S₂ = 698.90) 1-27 m/z = 612.26(C₄₆H₃₂N₂ =612.76) 1-28 m/z = 769.26(C₅₅H₃₅N₃S = 769.95) 1-29 m/z =782.24(C₅₆H₃₄N₂OS = 782.95) 1-30 m/z = 943.39(C₇₁H₄₉N₃ = 944.19) 1-31m/z = 835.30(C₆₀H₄₁N₃S = 836.07) 1-32 m/z = 714.30(C₅₄H₃₈N₂ = 714.89)1-33 m/z = 805.31(C₅₉H₃₉N₃O = 805.96) 1-34 m/z = 803.33(C₆₀H₄₁N₃ =803.99) 1-35 m/z = 768.26(C₅₆H₃₆N₂S = 768.96) 1-36 m/z =767.33(C₅₈H₃₃D₅N₂ = 767.99) 1-37 m/z = 778.37(C₅₆H₅₀N₂Si = 779.12) 1-38m/z = 610.24(C₄₃H₃₁FN₂O = 610.73) 1-39 m/z = 749.24(C₅₀H₃₁N₅O₃ = 749.83)1-40 m/z = 769.26(C₅₅H₃₅N₃S = 769.97) 1-41 m/z = 742.24(C₅₄H₃₄N₂S =742.93) 1-42 m/z = 732.22(C₅₂H₃₂N₂OS = 732.89) 1-43 m/z =731.24(C₅₂H₃₃N₃S = 731.92) 1-44 m/z = 652.25(C₄₈H₃₂N₂O = 652.78) 1-45m/z = 679.30(C₅₀H₃₇N₃ = 679.87) 1-46 m/z = 642.30(C₄₈H₃₈N₂ = 642.83)1-47 m/z = 830.29(C₆₁H₃₈N₂O₂ = 830.99) 1-48 m/z = 907.36(C₆₇H₄₅N₃O =908.09) 1-49 m/z = 776.32(C₅₉H₄₀N₂ = 776.96) 1-50 m/z = 865.35(C₆₅H₄₃N₃= 866.06) 1-51 m/z = 936.35(C₇₂H₄₄N₂ = 937.13) 1-52 m/z =688.29(C₅₂H₃₆N₂ = 688.86) 1-53 m/z = 794.28(C₅₈H₃₈N₂S = 795.00) 1-54 m/z= 884.29(C₆₄H₄₀N₂OS = 885.08) 1-55 m/z = 738.30(C₅₆H₃₈N₂ = 738.91) 1-56m/z = 792.31(C₅₉H₄₀N₂O = 792.98) 1-57 m/z = 907.30(C₆₆H₄₁N₃S = 908.14)1-58 m/z = 879.32(C₆₅H₄₁N₃O = 880.04) 1-59 m/z = 795.37(C₆₀H₃₇D₅N₂ =796.02) 1-60 m/z = 864.35(C₆₆H₄₄N₂ = 865.07) 2-1 m/z = 588.26(C₄₄H₃₂N₂ =588.74) 2-2 m/z = 816.35(C₆₂H₄₄N₂ = 817.05) 2-3 m/z = 792.35(C₆₀H₄₄N₂ =793.03) 2-4 m/z = 763.30(C₅₇H₃₇N₃ = 763.94) 2-5 m/z = 700.37(C₅₂H₂₈D₁₀N₂= 700.95) 2-6 m/z = 730.33(C₅₅H₄₂N₂ = 730.96) 2-7 m/z =877.44(C₆₆H₄₃D₇N₂ = 878.18) 2-8 m/z = 876.35(C₆₄H₄₈N₂S = 877.16) 2-9 m/z= 952.48(C₇₂H₆₀N₂ = 953.29) 2-10 m/z = 828.35(C₆₃H₄₄N₂ = 829.06) 2-11m/z = 863.33(C₆₂H₄₅N₃S = 864.12) 2-12 m/z = 981.41(C₇₄H₅₁N₃ = 982.24)2-13 m/z = 816.31(C₆₁H₄₀N₂O = 817.00) 2-14 m/z = 770.28(C₅₆H₃₈N₂S =770.99) 2-15 m/z = 794.29(C₅₈H₃₈N₂O₂ = 794.95) 2-16 m/z =852.26(C₆₀H₄₀N₂S₂ = 853.10) 2-17 m/z = 912.18(C₆₀H₃₆N₂S₄ = 913.20) 2-18m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.10) 2-19 m/z = 905.38(C₆₈H₄₇N₃ = 906.15)2-20 m/z = 935.33(C₆₈H₄₅N₃S = 936.19) 2-21 m/z = 709.26(C₅₀H₃₅N₃S =709.91) 2-22 m/z = 800.2 3(C₅₆H₃₆N₂S₂ = 801.04) 2-23 m/z =818.34(C₆₀H₄₂N₄ = 819.02) 2-24 m/z = 818.34(C₆₀H₄₂N₄ = 819.02) 2-25 m/z= 650.35(C₄₈H₂₆D₁₀N₂ = 650.89) 2-26 m/z = 664.29(C₅₀H₃₆N₂ = 664.85) 2-27m/z = 760.25(C₅₄H₃₆N₂OS = 760.96) 2-28 m/z = 664.29(C₅₀H₃₆N₂ = 664.85)2-29 m/z = 740.32(C₅₆H₄₀N₂ = 740.95) 2-30 m/z = 878.37(C₆₇H₄₆N₂ =879.12) 2-31 m/z = 911.33(C₆₆H₄₅N₃S = 912.17) 2-32 m/z = 664.29(C₅₀H₃₆N₂= 664.85) 2-33 m/z = 844.31(C₆₂H₄₀N₂O₂ = 844.99) 2-34 m/z =664.29(C₅₀H₃₆N₂ = 664.85) 2-35 m/z = 664.29(C₅₀H₃₆N₂ = 664.85) 2-36 m/z= 820.31(C₆₀H₄₀N₂O₂ = 820.99) 2-37 m/z = 640.29(C₄₈H₃₆N₂ = 640.83) 2-38m/z = 881.38(C₆₆H₄₇N₃ = 882.10) 2-39 m/z = 764.32(C₅₈H₄₀N₂ = 764.97)2-40 m/z = 648.35(C₄₈H₄₄N₂ = 648.89) 2-41 m/z = 908.39(C₆₇H₄₈N₄ =909.15) 2-42 m/z = 538.24(C₄₀H₃₀N₂ = 538.69) 2-43 m/z = 588.26(C₄₄H₃₂N₂= 588.75) 2-44 m/z = 588.26(C₄₄H₃₂N₂ = 588.75) 2-45 m/z =764.32(C₅₈H₄₀N₂ = 764.97) 2-46 m/z = 846.31(C₆₂H₄₂N₂S = 847.09) 2-47 m/z= 677.28(C₅₀H₃₅N₃ = 677.85 2-48 m/z = 627.27(C₄₆H₃₃N₃ = 627.79) 2-49 m/z= 814.21(C₅₆H₃₄N₂OS₂ = 815.02) 2-50 m/z = 720.26(C₅₂H₃₆N₂S = 720.93)2-51 m/z = 748.27(C₅₂H₃₆N₄S = 748.95) 2-52 m/z = 744.26(C₅₄H₃₆N₂S =744.96) 2-53 m/z = 774.27(C₅₅H₃₈N₂OS = 774.98) 2-54 m/z =731.33(C₅₄H₄₁N₃ = 731.94) 2-55 m/z = 670.24(C₄₈H₃₄N₂S = 670.87) 2-56 m/z= 866.24(C₆₀H₃₈N₂OS₂ = 867.10) 2-57 m/z = 698.20(C₄₈H₃₀N₂O₂S = 698.84)2-58 m/z = 850.34(C₆₂H₄₆N₂S = 851.12) 2-59 m/z = 782.30(C₅₆H₃₈N₄ =782.95) 2-60 m/z = 729.31(C₅₄H₃₉N₃ = 729.93) 2-61 m/z = 936.44(C₇₁H₅₆N₂= 937.24) 2-62 m/z = 744.28(C₅₄H₃₆N₂O₂ = 744.89) 2-63 m/z =792.35(C₆₀H₄₄N₂ = 793.03) 2-64 m/z = 756.35(C₅₇H₄₄N₄ = 756.99) 2-65 m/z= 694.24(C₅₀H₃₄N₂S = 694.90) 2-66 m/z = 852.26(C₆₀H₄₀N₂S₂ = 853.11) 2-67m/z = 922.40(C₆₈H₅₀N₄ = 923.18) 2-68 m/z = 631.27(C₄₄H₃₃N₅ = 631.78)2-69 m/z = 626.24(C₄₃H₃₁FN₂O₂ = 626.73) 2-70 m/z = 723.40(C₅₁H₄₁D₇N₂Si =724.09)

Synthesis Examples 2

I. Synthesis of Formula (2)

The final product 2 represented by Formula (2) of the present inventionis prepared by reacting Sub 3 and Sub 4 as shown in the followingReaction Scheme 6.

Synthesis Example of Sub 3

Sub 3 of Reaction Scheme 6 can be synthesized by the reaction path ofthe following Reaction Scheme 7, but is not limited thereto.

Synthesis Example of Sub 3-1

(1) Synthesis of Sub 3-I-1

After 6-bromobenzo[b]naphtha[1,2-d]thiophene (60 g, 191.56 mmol),bis(pinacolato)diboron (53.51 g, 210.72 mmol), KOAc (56.40 g, 574.69mmol), PdCl₂(dppf) (4.21 g, 5.75 mmol) were dissolved in DMF (1207 mL),and refluxed at 120° C. for 12 hours. When the reaction was completed,the temperature of the reaction was cooled to room temperature,extracted with CH₂Cl₂ and wiped with water. The organic layer was driedover MgSO₄ and concentrated. The resulting compound was recrystallizedby CH₂Cl₂ and methanol solvent to obtain the product. (53.14 g, 77%)

(2) Synthesis of Sub 3-II-1

Sub 3-I-1 (53.14 g, 147.50 mmol), 1-bromo-2-nitrobenzene (29.80 g,147.50 mmol), K₂CO₃ (61.16 g, 442.49 mmol), Pd(PPh₃)₄ (5.11 g, 4.42mmol) were added in a round bottom flask and THF (649 mL) and water (324mL) were added to dissolve and refluxed at 80° C. for 12 hours. When thereaction was completed, the temperature of the reaction was cooled toroom temperature, extracted with CH₂Cl₂ and wiped with water.

The organic layer was dried over MgSO₄ and concentrated. The resultingcompound was separated by silicagel column chromatography to obtain theproduct. (41.94 g, 80%)

(3) Synthesis of Sub 3-1

Sub 3-II-1 (41.94 g, 118.00 mmol) and triphenylphosphine (77.38 g,295.01 mmol) were dissolved in o-dichlorobenzene (590 mL) and refluxedfor 24 hours. When the reaction was completed, the solvent was removedusing reduced pressure distillation. The resulting compound wasseparated by silicagel column chromatography and recrystallized toobtain the product. (19.85 g, 52%)

Synthesis of Sub 3-7

(1) Synthesis of Sub 3-I-27-bromo-11-phenyl-11H-benzo[a]carbazole (60 g, 161.17 mmol),bis(pinacolato)diboron (45.02 g, 177.29 mmol), KOAc (47.455 g, 483.52mmol), PdCl₂(dppf) (3.54 g, 4.84 mmol) and DMF (1015 mL) were carriedout in the same manner as in Sub 3-I-1 to give the product. (54.74 g,81%).(2) Synthesis of Sub 3-II-2

Sub 3-I-2 (54.74 g, 130.54 mmol), 1-bromo-2-nitrobenzene (26.37 g,130.54 mmol), K₂CO₃ (54.13 g, 391.62 mmol), Pd(PPh₃)₄ (4.53 g, 3.92mmol)), THF (574 ml) and water (287 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (44.91 g, 83%).

(3) Synthesis of Sub 3-7

Sub 3-II-2 (44.91 g, 108.36 mmol), triphenylphosphine (71.05 g, 270.89mmol) and o-dichlorobenzene (542 mL) were carried out in the same manneras in Sub 3-1 to give the product. (19.06 g, 46%).

Synthesis of Sub 3-13

(1) Synthesis of Sub 3-I-413-bromophenanthro[9,10-b]benzofuran (60 g, 172.81 mmol),bis(pinacolato)diboron (48.27 g, 190.09 mmol), KOAc (50.88 g, 518.42mmol), PdCl₂(dppf) (3.79 g, 5.18 mmol) and DMF (1088 mL) were carriedout in the same manner as in Sub 3-I-1 to give the product. (50.42 g,74%).(2) Synthesis of Sub 3-II-3

Sub 3-I-3 (50.42 g, 127.88 mmol), 1-bromo-2-nitrobenzene (25.83 g,127.88 mmol), K₂CO₃ (53.02 g, 383.64 mmol), Pd(PPh₃)₄ (4.43 g, 3.84mmol), THF (562 ml) and water (281 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (38.84 g, 78%).

(3) Synthesis of Sub 3-13

Sub 3-II-3 (38.84 g, 99.74 mmol), triphenylphosphine (65.40 g, 249.35mmol), o-dichlorobenzene (499 ml) were carried out in the same manner asin Sub 3-1 to give Sub 3-13. (15.33 g, 43%).

Synthesis of Sub 3-20

(1) Synthesis of Sub 3-I-412-bromo-13,13-dimethyl-13H-benzo[b]fluorene (60 g, 160.73 mmol),bis(pinacolato)diboron (44.90 g, 176.81 mmol), KOAc (47.32 g, 482.20mmol), PdCl₂(dppf) (3.53 g, 4.82 mmol) and DMF (1013 mL) were carriedout in the same manner as in Sub 3-I-1 to give the product. (47.30 g,70%).(2) Synthesis of Sub 3-II-4

Sub 3-I-4 (47.30 g, 112.52 mmol), 2-bromo-3-nitronaphthalene (28.36 g,112.52 mmol), K₂CO₃ (46.66 g, 337.57 mmol), Pd(PPh₃)₄ (3.90 g, 3.38mmol), THF (495 ml)) and water (248 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (39.29 g, 75%).

(3) Synthesis of Sub 3-20

Sub 3-II-4 (39.29 g, 84.39 mmol), triphenylphosphine (55.34 g, 210.99mmol), o-dichlorobenzene (543 ml) were carried out in the same manner asin Sub 3-1 to give the product Sub 3-13. (14.27 g, 39%).

Synthesis of Sub 3-26

(1) Synthesis of Sub 3-I-54-bromo-11,11-dimethyl-11H-benzo[b]fluorene (60 g, 185.63 mmol),bis(pinacolato)diboron (51.85 g, 204.19 mmol), KOAc (54.65 g, 556.88mmol), PdCl₂(dppf) (4.07 g, 5.57 mmol) were carried out in the samemanner as in Sub 3-I-1 to give the product. (49.49 g, 72%).(2) Synthesis of Sub 3-II-5

Sub 3-I-5 (49.49 g, 133.65 mmol), 2-bromo-1-nitronaphthalene (33.69 g,133.65 mmol), K₂CO₃ (55.41 g, 400.95 mmol), Pd(PPh₃)₄ (4.63 g, 4.01mmol), THF (588 mL) and water (294 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (41.09 g, 74%).

(3) Synthesis of Sub 3-26

Sub 3-II-5 (41.09 g, 98.90 mmol), triphenylphosphine (64.85 g, 247.24mmol), o-dichlorobenzene (494 mL) were carried out in the same manner asin Sub 3-1 to give the product. (15.55 g, 41%).

Synthesis of Sub 3-39

(1) Synthesis of Sub 3-I-611-bromo-7-phenyl-7H-benzo[c]carbazole (60 g, 161.17 mmol),bis(pinacolato)diboron (45.02 g, 177.29 mmol), KOAc (47.45 g, 483.52mmol), PdCl₂(dppf) (3.54 g, 4.84 mmol), DMF (1015 ml) were carried outin the same manner as in Sub 3-I-1 to give the product. (48.66 g, 72%).(2) Synthesis of Sub 3-II-6

Sub 3-I-6 (48.66 g, 116.04 mmol), 2-bromo-3-nitronaphthalene (29.25 g,116.04 mmol), K₂CO₃ (48.11 g, 348.13 mmol), Pd(PPh₃)₄ (4.02 g, 3.48mmol), THF (511 mL) and water (255 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (37.73 g, 70%).

(3) Synthesis of Sub 3-39

Sub 3-II-6 (37.73 g, 81.22 mmol), triphenylphosphine (53.26 g, 203.06mmol), o-dichlorobenzene (406 mL) were carried out in the same manner asin Sub 3-1 to give the product. (15.46 g, 44%).

Synthesis of Sub 3-45

(1) Synthesis of Sub 3-I-74-bromonaphtho[2,3-b]benzofuran (60 g, 201.92 mmol),bis(pinacolato)diboron (56.40 g, 222.11 mmol), KOAc (59.45 g, 605.75mmol), PdCl₂(dppf) (4.43 g, 6.06 mmol), DMF (1272 ml) were carried outin the same manner as in Sub 3-I-1 to give the product. (54.21 g, 78%).(2) Synthesis of Sub 3-II-7

Sub 3-I-7 (54.21 g, 157.49 mmol), 2-bromo-1-nitronaphthalene (39.70 g,157.49 mmol), K₂CO₃ (65.30 g, 472.46 mmol), Pd(PPh₃)₄ (5.46 g, 4.72mmol), THF (693 mL), and water (346 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (44.77 g, 73%).

(3) Synthesis of Sub 3-45

Sub 3-II-7 (44.77 g, 114.97 mmol), triphenylphosphine (75.39 g, 287.42mmol), o-dichlorobenzene (575 mL) were carried out in the same manner asin Sub 3-1 to give the product. (15.61 g, 38%).

Synthesis of Sub 3-60

(1) Synthesis of Sub 3-I-86-bromobenzo[b]naphtho[1,2-d]thiophene (60 g, 191.56 mmol),bis(pinacolato)diboron (53.51 g, 210.72 mmol), KOAc (56.40 g, 574.69mmol), PdCl₂(dppf) (4.21 g, 5.75 mmol), DMF (1207 ml) were carried outin the same manner as in Sub 3-I-1 to give the product. (52.45 g, 76%).(2) Synthesis of Sub 3-II-8

Sub 3-I-8 (52.45 g, 55.51 mmol), 1-bromo-2-nitronaphthalene (52.45 g,145.58 mmol), K₂CO₃ (60.36 g, 436.74 mmol), Pd(PPh₃)₄ (5.05 g, 4.37mmol), THF (641 mL) and water (320 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (46.63 g, 79%).

(3) Synthesis of Sub 3-61

Sub 3-II-8 (46.63 g, 115.00 mmol), triphenylphosphine (75.41 g, 287.51mmol), o-dichlorobenzene (575 mL) were carried out in the same manner asin Sub 3-1 to give the product. (18.04 g, 42%).

Synthesis of Sub 3-62

(1) Synthesis of Sub 3-I-91-bromo-9,9-dimethyl-9H-fluorene (60 g, 219.64 mmol),bis(pinacolato)diboron (61.35 g, 241.61 mmol), KOAc (64.67 g, 658.93mmol), PdCl₂(dppf) (4.82 g, 6.59 mmol), DMF (1384 ml) were carried outin the same manner as in Sub 3-I-1 to give the product. (51.35 g, 73%).(2) Synthesis of Sub 3-II-9

Sub 3-I-9 (51.35 g, 160.35 mmol), 9-bromo-10-nitrophenanthrene (48.45 g,160.35 mmol), K₂CO₃ (66.49 g, 481.05 mmol), Pd(PPh₃)₄ (5.56 g, 4.81mmol), THF (706 mL),) and water (353 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (45.97 g, 69%).

(3) Synthesis of Sub 3-62

Sub 3-II-9 (45.97 g, 110.64 mmol), triphenylphosphine (72.55 g, 276.60mmol), o-dichlorobenzene (553 mL) were carried out in the same manner asin Sub 3-1 to give the product. (15.70 g, 37%).

Synthesis of Sub 3-75

(1) Synthesis of Sub 3-II-10

Sub 3-I-8 (45 g, 124.90 mmol), 3-bromo-4-nitro-1,1′-biphenyl (35.74 g,124.90 mmol), K₂CO₃ (51.79 g, 374.71 mmol), Pd(PPh₃)₄ (4.33 g, 3.75mmol), THF (550 ml) and water (275 ml) were carried out in the samemanner as in Sub 3-II-1 to give the product. (38.27 g, 71%).

(2) Synthesis of Sub 3-75

Sub 3-II-10 (38.27 g, 88.69 mmol), triphenylphosphine (58.16 g, 221.72mmol), o-dichlorobenzene (443 mL) were carried out in the same manner asin Sub 3-1 to give the product. (14.53 g, 41%)

Synthesis of Sub 3-84

(1) Synthesis of Sub 3-I-107-bromonaphtho[1,2-b]benzofuran (60 g, 201.92 mmol),bis(pinacolato)diboron (56.40 g, 222.11 mmol), KOAc (59.45 g, 605.75mmol), PdCl₂(dppf) (4.43 g, 6.06 mmol), DMF (1272 ml) were carried outin the same manner as in Sub 3-I-1 to give the product. (49.35 g, 71%)(2) Synthesis of Sub 3-II-11

Sub 3-I-10 (34 g, 98.77 mmol),10-(3-bromo-4-nitrophenyl)-7-phenyl-7H-benzo[c]carbazole (48.73 g, 98.77mmol), K₂CO₃ (40.95 g, 296.32 mmol), Pd(PPh₃)₄ (3.42 g, 2.96 mmol), THF(435 ml) and water (217 ml) were carried out in the same manner as inSub 3-II-1 to give the product. (46.10 g, 74%).

(3) Synthesis of Sub 3-84

Sub 3-II-11 (46 g, 72.93 mmol), triphenylphosphine (47.83 g, 182.34mmol), o-dichlorobenzene (365 mL) were carried out in the same manner asin Sub 3-1 to give the product. (17.90 g, 41%)

Examples of Sub 3 include, but are not limited to, the followings.

TABLE 4 compound FD-MS compound FD-MS Sub 3-1 m/z = 323.08(C₂₂H₁₃NS =323.41) Sub 3-2 m/z = 323.08(C₂₂H₁₃NS = 323.41) Sub 3-3 m/z =307.10(C₂₂H₁₃NO = 307.35) Sub 3-4 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub3-5 m/z = 333.15(C₂₅H₁₉N = 333.43) Sub 3-6 m/z = 382.15(C₂₈H₁₈N₂ =382.46) Sub 3-7 m/z = 382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-8 m/z =323.08(C₂₂H₁₃NS = 323.41) Sub 3-9 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub3-10 m/z = 383.17(C₂₉H₂₁N = 383.49) Sub 3-11 m/z = 373.09(C₂₆H₁₅NS =373.47) Sub 3-12 m/z = 323.08(C₂₂H₁₃NS = 323.41) Sub 3-13 m/z =357.12(C₂₆H₁₅NO = 357.41) Sub 3-14 m/z = 333.15(C₂₅H₁₉N = 333.43) Sub3-15 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3-16 m/z = 357.12(C₂₆H₁₅NO =357.41) Sub 3-17 m/z = 383.17(C₂₉H₂₁N = 383.49) Sub 3-18 m/z =373.09(C₂₆H₁₅NS = 373.47) Sub 3-19 m/z = 407.13(C₃₀H₁₇NO = 407.47) Sub3-20 m/z = 433.18(C₃₃H₂₃N = 433.55) Sub 3-21 m/z = 373.09(C₂₆H₁₅NS =373.47) Sub 3-22 m/z = 357.12(C₂₆H₁₅NO = 357.41) Sub 3-23 m/z =662.25(C₄₈H₃₀N₄ = 662.80) Sub 3-24 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub3-25 m/z = 357.12(C₂₆H₁₅NO = 357.41) Sub 3-26 m/z = 383.17(C₂₉H₂₁N =383.49) Sub 3-27 m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub 3-28 m/z =323.08(C₂₂H₁₃NS = 323.41) Sub 3-29 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub3-30 m/z = 455.17(C₃₅H₂₁N = 455.56) Sub 3-31 m/z = 432.16(C₃₂H₂₀N₂ =432.53) Sub 3-32 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3-33 m/z =357.12(C₂₆H₁₅NO = 357.41) Sub 3-34 m/z = 383.17(C₂₉H₂₁N = 383.49) Sub3-35 m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub 3-36 m/z = 373.09(C₂₆H₁₅NS =373.47) Sub 3-37 m/z = 357.12(C₂₆H₁₅NO = 357.41) Sub 3-38 m/z =383.17(C₂₉H₂₁N = 383.49) Sub 3-39 m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub3-40 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3-41 m/z = 357.12(C₂₆H₁₅NO =357.41) Sub 3-42 m/z = 505.18(C₃₉H₂₃N = 505.62) Sub 3-43 m/z =382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-44 m/z = 323.08(C₂₂H₁₃NS = 323.41) Sub3-45 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub 3-46 m/z = 333.15(C₂₅H₁₉N =333.43) Sub 3-47 m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub 3-48 m/z =323.08(C₂₂H₁₃NS = 323.41) Sub 3-49 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub3-50 m/z = 457.18(C₃₅H₂₃N = 457.58) Sub 3-51 m/z = 432.16(C₃₂H₂₀N₂ =432.53) Sub 3-52 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3-53 m/z =357.12(C₂₆H₁₅NO = 357.41) Sub 3-54 m/z = 383.17(C₂₉H₂₁N = 383.49) Sub3-55 m/z = 616.17(C₄₂H₂₄N₄S = 616.74) Sub 3-56 m/z = 323.08(C₂₂H₁₃NS =323.41) Sub 3-57 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub 3-58 m/z =373.09(C₂₆H₁₅NS = 373.47) Sub 3-59 m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub3-60 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3-61 m/z = 357.12(C₂₆H₁₅NO =357.41) Sub 3-62 m/z = 383.17(C₂₉H₂₁N = 383.49) Sub 3-63 m/z =432.16(C₃₂H₂₀N₂ = 432.53) Sub 3-64 m/z = 432.16(C₃₂H₂₀N₂ = 432.53) Sub3-65 m/z = 548.23(C₄₁H₂₈N₂ = 548.69) Sub 3-66 m/z = 507.20(C₃₉H₂₅N =507.64) Sub 3-67 m/z = 383.17(C₂₉H₂₁N = 383.49) Sub 3-68 m/z =373.09(C₂₆H₁₅NS = 373.47) Sub 3-69 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub3-70 m/z = 333.15(C₂₅H₁₉N = 333.43) Sub 3-71 m/z = 383.17(C₂₉H₂₁N =383.49) Sub 3-72 m/z = 373.09(C₂₆H₁₅NS = 373.47) Sub 3-73 m/z =307.10(C₂₂H₁₃NO = 307.35) Sub 3-74 m/z = 333.15(C₂₅H₁₉N = 333.43) Sub3-75 m/z = 382.15(C₂₈H₁₈N₂ = 382.47) Sub 3-76 m/z = 490.15(C₃₄H₂₂N₂S =490.62) Sub 3-77 m/z = 468.11(C₃₁H₁₇FN₂S = 468.55) Sub 3-78 m/z =564.17(C₄₀H₂₄N₂S = 564.71) Sub 3-79 m/z = 555.11(C₃₈H₂₁NS₂ = 555.71) Sub3-80 m/z = 363.11(C₂₅H₁₇NS = 363.48) Sub 3-81 m/z = 692.20(C₄₈H₂₈N₄S =692.84) Sub 3-82 m/z = 337.11(C₂₃H₁₅NO₂ = 337.38) Sub 3-83 m/z =524.19(C₃₈H₂₄N₂O = 524.62) Sub 3-84 m/z = 598.20(C₄₄H₂₆N₂O = 598.71) Sub3-85 m/z = 538.18(C₃₇H₂₂N₄O = 538.61) Sub 3-86 m/z = 438.21(C₃₂H₂₆N₂ =438.57) Sub 3-87 m/z = 574.24(C₄₃H₃₀N₂ = 574.73) Sub 3-88 m/z =598.20(C₄₄H₂₆N₂O = 598.71) Sub 3-89 m/z = 699.23(C₅₁H₂₉N₃O = 699.81) Sub3-90 m/z = 307.10(C₂₂H₁₃NO = 307.35) Sub 3-91 m/z = 357.12(C₂₆H₁₅NO =357.41)

Synthesis Example of Sub 4

Sub 4 of Scheme 6 can be synthesized by the reaction path of Scheme 7below, but is not limited thereto.

At this time, Hal⁵=I, Br, Cl; Hal⁶=Br, Cl

Synthesis of Sub 4-35

(1) Synthesis of Sub 4-I-1

The starting material, 1-amino-2-naphthoic acid (CAS Registry Number:4919-43-1) (75.11 g, 401.25 mmol), was placed in a round bottom flaskwith urea (CAS Registry Number: 57-13-6) (168.69 g, 2808.75 mmol) andstirred at 160° C. After confirming the reaction by TLC, the reactionmixture was cooled to 100° C., water (200 ml) was added, and the mixturewas stirred for 1 hour. When the reaction was completed, the resultingsolid was filtered under reduced pressure, washed with water, and thendried to obtain 63.86 g (yield: 75%) of the product.

(2) Synthesis of Sub 4-II-1

Sub 4-I-1 (63.86 g, 300.94 mmol) was dissolved in POCl₃ (200 ml) at roomtemperature in a round bottom flask, and N, N-Diisopropylethylamine(97.23 g, 752.36 mmol) was slowly added dropwise thereto, followed bystirring at 90° C. After the reaction was completed, the reactionmixture was concentrated, and then ice water (500 ml) was added thereto,followed by stirring at room temperature for 1 hour. The resulting solidwas filtered under reduced pressure and dried to obtain 67.47 g (yield:90%) of the product.

(3) Synthesis of Sub 4-35

After Sub 4-II-1 (67.47 g, 270.86 mmol) was dissolved in THF (950 ml) ina round bottom flask, 4,4,5,5-tetramethyl-2-phenyl-1,3,2-dioxaborolane(CAS Registry Number: 24388-23-6) (60.80 g, 297.94 mmol), Pd(PPh₃)₄(12.52 g, 10.83 mmol), K₂CO₃ (112.30 g, 812.57 mmol) and water (475 mL)were added to dissolve and stirred at 90° C. After the reaction wascompleted, the reaction mixture was extracted with CH₂Cl₂ and water. Theorganic layer was dried over MgSO₄ and concentrated. The resultingcompound was purified by silicagel column and recrystallized to obtain44.89 g (yield: 57%) of the product.

Synthesis of Sub 4-40

Sub 4-II-1 (19 g, 76.28 mmol),2-(dibenzo[b,d]furan-2-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (CASRegistry Number: 947770-80-1) (22.44 g, 76.28 mmol), Pd(PPh₃)₄ (1.32 g,1.14 mmol), K₂CO₃ (15.81 g, 114.42 mmol), THF (336 ml) and water (168ml) were added and carried out in the same manner as in Sub 4-35 to givethe product. (15.69 g, 54%).

Synthesis of Sub 4-43

2,4-dichlorobenzo[4,5]thieno[3,2-d]pyrimidine (CAS Registry Number:160199-05-3) (32.01 g, 125.47 mmol),4,4,5,5-tetramethyl-2-(naphthalen-1-yl)-1,3,2-dioxaborolane (CASRegistry Number: 68716-52-9) (35.07 g, 138.02 mmol), Pd(PPh₃)₄ (5.80 g,5.02 mmol), K₂CO₃ (52.02 g, 376.41 mmol), THF (440 ml) and water (220ml) were added and carried out in the same manner as in Sub 4-35 to givethe product. (19.58 g, 45%).

The compounds belonging to Sub 4 may be, but not limited to, thefollowing compounds, and Table 5 shows FD-MS (Field Desorption-MassSpectrometry) values of Sub 4 compounds.

Examples of Sub 4 include, but are not limited to, the followings.

TABLE 5 compound FD-MS compound FD-MS Sub 4-1 m/z = 155.96(C₆H₅Br =157.01) Sub 4-2 m/z = 205.97(C₁₀H₇Br = 207.07) Sub 4-3 m/z =205.97(C₁₀H₇Br = 207.07) Sub 4-4 m/z = 231.99(C₁₂H₉Br = 233.11) Sub 4-5m/z = 231.99(C₁₂H₉Br = 233.11) Sub 4-6 m/z = 308.02(C₁₈H₁₃Br = 309.21)Sub 4-7 m/z = 255.99(C₁₄H₉Br = 257.13) Sub 4-8 m/z = 306.00(C₁₈H₁₁Br =307.19) Sub 4-9 m/z = 272.02(C₁₅H₁₃Br = 273.17) Sub 4-10 m/z =321.02(C₁₈H₁₂BrN = 322.21) Sub 4-11 m/z = 261.95(C₁₂H₇BrS = 263.15) Sub4-12 m/z = 245.97(C₁₂H₇BrO = 247.09) Sub 4-13 m/z = 156.95(C₅H₄BrN =158.00) Sub 4-14 m/z = 156.95(C₅H₄BrN = 158.00) Sub 4-15 m/z =157.95(C₄H₃BrN₂ = 158.99) Sub 4-16 m/z = 266.06(C₁₆H₁₁ClN₂ = 266.72) Sub4-17 m/z = 267.06(C₁₅H₁₀ClN₃ = 267.72) Sub 4-18 m/z = 266.06(C₁₆H₁₁ClN₂= 266.72) Sub 4-19 m/z = 316.08(C₂₀H₁₃ClN₂ = 316.79) Sub 4-20 m/z =310.01(C₁₆H₁₁BrN₂ = 311.18) Sub 4-21 m/z = 311.01(C₁₅H₁₀BrN₃ = 312.17)Sub 4-22 m/z = 311.01(C₁₅H₁₀BrN₃ = 312.17) Sub 4-23 m/z =386.04(C₂₂H₁₅BrN₂ = 387.28) Sub 4-24 m/z = 386.04(C₂₂H₁₅BrN₂ = 387.28)Sub 4-25 m/z = 387.04(C₂₁H₁₄BrN₃ = 388.27) Sub 4-26 m/z =348.03(C₁₉H₁₃BrN₂ = 349.23) Sub 4-27 m/z = 273.13(C₁₃H₉BrN₂ = 273.13)Sub 4-28 m/z = 240.05(C₁₄H₉ClN₂ = 240.69 Sub 4-29 m/z =290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 4-30 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75)Sub 4-31 m/z = 316.08(C₂₀H₁₃ClN₂ = 316.79) Sub 4-32 m/z =296.11(C₁₈H₁₇ClN₂ = 296.80) Sub 4-33 m/z = 245.08(C₁₄H₄D₅ClN₂ = 245.72)Sub 4-34 m/z = 290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 4-35 m/z =290.06(C₁₈H₁₁ClN₂ = 290.75) Sub 4-36 m/z = 340.08(C₂₂H₁₃ClN₂ = 340.81)Sub 4-37 m/z = 340.08(C₂₂H₁₃ClN₂ = 340.81) Sub 4-38 m/z =396.05(C₂₄H₁₃ClN₂S = 396.89) Sub 4-39 m/z = 371.12(C₂₄H₁₀D₅ClN₂ =371.88) Sub 4-40 m/z = 380.07(C₂₄H₁₃ClN₂O = 380.83) Sub 4-41 m/z =308.05(C₁₈H₁₀ClFN₂ = 308.74) Sub 4-42 m/z = 296.02(C₁₆H₉ClN₂S = 296.77)Sub 4-43 m/z = 346.03(C₂₀H₁₁ClN₂S = 346.83) Sub 4-44 m/z =372.05(C₂₂H₁₃ClN₂S = 372.87) Sub 4-45 m/z = 432.10(C₂₈H₁₇ClN₂O = 432.91)Sub 4-46 m/z = 358.09(C₂₂H₁₅ClN₂O = 358.83) Sub 4-47 m/z =280.04(C₁₆H₉ClN₂O = 280.71) Sub 4-48 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.24)Sub 4-49 m/z = 460.06(C₂₈H₁₇BrN₂ = 461.36) Sub 4-50 m/z =416.00(C₂₂H₁₃BrN₂S = 417.32) Sub 4-51 m/z = 516.03(C₃₀H₁₇BrN₂S = 517.44)Sub 4-52 m/z = 340.08(C₂₂H₁₃ClN₂ = 340.81) Sub 4-53 m/z =346.03(C₂₀H₁₁ClN₂S = 346.83) Sub 4-54 m/z = 331.05(C₁₉H₁₀ClN₃O = 331.76)Sub 4-55 m/z = 360.03(C₂₀H₁₃BrN₂ = 361.24) Sub 4-56 m/z =492.03(C₂₈H₁₇BrN₂S = 493.42) Sub 4-57 m/z = 316.08(C₂₀H₁₃ClN₂ = 316.79)Sub 4-58 m/z = 392.11(C₂₆H₁₇ClN₂ = 392.89) Sub 4-59 m/z =316.08(C₂₀H₁₃ClN₂ = 316.79) Sub 4-60 m/z = 367.09(C₂₃H₁₄ClN₃ = 367.84)Sub 4-61 m/z = 280.04(C₁₆H₉ClN₂O = 280.71) Sub 4-62 m/z =463.07(C₂₇H₁₈BrN₃ = 464.37)Synthesis of Final Products 2

After Sub 3 (1 eq.) was dissolved in toluene in a round bottom flask,Sub 4 (1 eq.), Pd₂(dba)₃ (0.03 eq.), P(t-Bu)₃ (0.1 eq.), NaOt-Bu (3 eq.)were added and stirred at 100° C. When the reaction was complete, thereaction mixture was extracted with CH₂Cl₂ and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallization toobtain the Final products.

Synthesis Example of 3-1

Sub 3-7 (5.3 g, 16.39 mmol) was dissolved in toluene (172 mL) in a roundbottom flask, and Sub 4-1 (4.86 g, 16.39 mmol), Pd₂(dba)₃ (0.45 g, 0.49mmol), P(t-Bu)₃ (0.20 g, 0.98 mmol), NaOt-Bu (4.72 g, 49.16 mmol) wereadded and stirred at 100° C. After the reaction was completed, thereaction mixture was extracted with CH₂Cl₂ and water. The organic layerwas dried over MgSO₄ and concentrated. The resulting compound wasseparated by silicagel column chromatography and recrystallized toobtain 7.56 g of the product. (yield: 79%)

Synthesis Example of 3-6

Sub 3-1 (6.21 g, 19.20 mmol), toluene (202 ml), Sub 4-28 (5.48 g, 19.20mmol), Pd₂(dba)₃ (0.53 g, 0.58 mmol), P(t-Bu)₃ (0.23 g, 1.15 mmol),NaOt-Bu (5.54 g, 57.60 mmol) were carried out in the same manner as in3-1 to give the product. (7.50 g, 74%).

Synthesis Example of 3-7

Sub 3-1 (5.85 g, 18.09 mmol), toluene (190 ml), Sub 4-42 (5.37 g, 18.09mmol), Pd₂(dba)₃ (0.50 g, 0.54 mmol), P(t-Bu)₃ (0.22 g, 1.09 mmol),NaOt-Bu (5.21 g, 54.27 mmol) were carried out in the same manner as in3-1 to give the product. (7.50 g, 71%).

Synthesis Example of 3-8

Sub 3-1 (6.2 g, 19.17 mmol), toluene (201 ml), Sub 4-35 (5.57 g, 19.17mmol), Pd₂(dba)₃ (0.53 g, 0.58 mmol), P(t-Bu)₃ (0.23 g, 0.15 mmol),NaOt-Bu (5.53 g, 57.51 mmol) were carried out in the same manner as in3-1 to give the product. (7.53 g, 68%).

Synthesis Example of 3-11

Sub 3-13 (6.4 g, 17.91 mmol), toluene (188 ml), Sub 4-6 (5.54 g, 17.91mmol), Pd₂(dba)₃ (0.49 g, 0.54 mmol), P(t-Bu)₃ (0.22 g, 1.07 mmol),NaOt-Bu (5.16 g, 53.72 mmol) were carried out in the same manner as in3-1 to give the product. (7.55 g, 72%).

Synthesis Example of 3-16

Sub 3-17 (6.9 g, 17.99 mmol), toluene (189 ml), Sub 4-10 (5.8 g, 17.99mmol), Pd₂(dba)₃ (0.49 g, 0.54 mmol), P(t-Bu)₃ (0.22 g, 1.08 mmol),NaOt-Bu (5.19 g, 53.98 mmol) were carried out in the same manner as in3-1 to give the product. (7.53 g, 67%).

Synthesis Example of 3-17

Sub 3-64 (7.6 g, 17.57 mmol), toluene (184 ml), Sub 4-11 (4.62 g, 17.57mmol), Pd₂(dba)₃ (0.48 g, 0.53 mmol), P(t-Bu)₃ (0.21 g, 1.05 mmol),NaOt-Bu (5.07 g, 52.71 mmol) were carried out in the same manner as in3-1 to give the product. (7.56 g, 70%).

Synthesis Example of 3-47

Sub 3-41 (7 g, 19.59 mmol), toluene (206 ml), Sub 4-47 (5.50 g, 19.59mmol), Pd₂(dba)₃ (0.54 g, 0.59 mmol), P(t-Bu)₃ (0.24 g, 1.18 mmol),NaOt-Bu (5.65 g, 58.76 mmol) were carried out in the same manner as in3-1 to give the product. (7.54 g, 64%).

Synthesis Example of 3-52

Sub 3-46 (5.8 g, 17.39 mmol), toluene (183 ml), Sub 4-24 (6.74 g, 17.39mmol), Pd₂(dba)₃ (0.48 g, 0.52 mmol), P(t-Bu)₃ (0.21 g, 1.04 mmol),NaOt-Bu (5.01 g, 52.18 mmol) were carried out in the same manner as in3-1 to give the product. (7.57 g, 68%).

Synthesis Example of 3-70

Sub 3-60 (6.50 g, 17.40 mmol), toluene (183 ml), Sub 4-36 (5.93 g, 17.40mmol), Pd₂(dba)₃ (0.48 g, 0.52 mmol), P(t-Bu)₃ (0.21 g, 1.04 mmol),NaOt-Bu (5.02 g, 52.21 mmol) were carried out in the same manner as in3-1 to give the product. (7.55 g, 64%).

Synthesis Example of 3-85

Sub 3-81 (7.7 g, 11.11 mmol), toluene (117 ml), Sub 4-5 (2.59 g, 11.11mmol), Pd₂(dba)₃ (0.31 g, 0.33 mmol), P(t-Bu)₃ (0.13 g, 0.67 mmol),NaOt-Bu (3.20 g, 33.34 mmol) were carried out in the same manner as in3-1 to give the product. (7.51 g, 80%).

Synthesis Example of 3-92

Sub 3-85 (7.2 g, 13.37 mmol), toluene (140 ml), Sub 4-35 (3.89 g, 13.37mmol), Pd₂(dba)₃ (0.37 g, 0.40 mmol), P(t-Bu)₃ (0.16 g, 0.80 mmol),NaOt-Bu (3.85 g, 40.10 mmol) were carried out in the same manner as in3-1 to give the product. (7.53 g, 71%).

Synthesis Example of 3-93

Sub 3-86 (6.2 g, 14.14 mmol), toluene (148 ml), Sub 4-58 (5.55 g, 14.14mmol), Pd₂(dba)₃ (0.39 g, 0.42 mmol), P(t-Bu)₃ (0.17 g, 0.85 mmol),NaOt-Bu (4.08 g, 42.41 mmol) were carried out in the same manner as in3-1 to give the product. (7.53 g, 67%).

Synthesis Example of 3-101

Sub 3-92 (7.17 g, 19.20 mmol) and Sub 4-63 (4.62 g, 19.20 mmol) werecarried out in the same manner as in 3-1 to give the product. (7.54 g,68%).

Synthesis Example of 3-107

Sub 3-93 (7.17 g, 19.20 mmol) and Sub 4-64 (6.85 g, 19.20 mmol) werecarried out in the same manner as in 3-1 to give the product. (8.12 g,61%).

Synthesis Example of 3-119

Sub 3-94 (7.17 g, 19.20 mmol) and Sub 4-65 (8.00 g, 19.20 mmol) werecarried out in the same manner as in 3-1 to give the product. (9.12 g,63%).

Synthesis Example of 3-122

Sub 3-92 (6.21 g, 19.20 mmol)

Sub 4-66 (6.54 g, 19.20 mmol) were carried out in the same manner as in3-1 to give the product. (7.71 g, 64%).

TABLE 6 compound FD-MS compound FD-MS 3-1 m/z = 458.18(C₃₄H₂₂N₂ =458.56) 3-2 m/z = 449.12(C₃₂H₁₉NS = 449.57) 3-3 m/z = 433.15(C₃₂H₁₉NO =433.51) 3-4 m/z = 535.23(C₄₁H₂₉N = 535.69) 3-5 m/z = 399.11(C₂₈H₁₇NS =399.51) 3-6 m/z = 527.15(C₃₆H₂₁N₃S = 527.65) 3-7 m/z = 583.12(C₃₈H₂₁N₃S₂= 583.73) 3-8 m/z = 577.16(C₄₀H₂₃N₃S = 577.71) 3-9 m/z =627.18(C₄₄H₂₅N₃S = 627.77) 3-10 m/z = 475.14(C₃₄H₂₁NS = 475.61) 3-11 m/z= 585.21(C₄₄H₂₇NO = 585.71) 3-12 m/z = 509.21(C₃₉H₂₇N = 509.65) 3-13 m/z= 509.19(C₃₇H₂₃N₃ = 509.61) 3-14 m/z = 451.11(C₃₀H₁₇N₃S = 451.55) 3-15m/z = 588.20(C₄₁H₂₄N₄O = 588.67) 3-16 m/z = 624.26(C₄₇H₃₂N₂ = 624.79)3-17 m/z = 614.18(C₄₄H₂₆N₂S = 614.77) 3-18 m/z = 449.12(C₃₂H₁₉NS =449.57) 3-19 m/z = 573.17(C₄₂H₂₃NO₂ = 573.65) 3-20 m/z = 664.26(C₄₈H₃₂N₄= 664.81) 3-21 m/z = 624.26(C₄₇H₃₂N₂ = 624.79) 3-22 m/z =603.18(C₄₂H₂₅N₃S = 603.74) 3-23 m/z = 664.23(C₄₇H₂₈N₄O = 664.77) 3-24m/z = 737.28(C₅₅H₃₅N₃ = 737.91) 3-25 m/z = 738.28(C₅₄H₃₄N₄ = 738.89)3-26 m/z = 679.21(C₄₈H₂₉N₃S = 679.84) 3-27 m/z = 625.22(C₄₅H₂₇N₃O =625.73) 3-28 m/z = 575.24(C₄₂H₂₉N₃ = 575.72) 3-29 m/z = 508.19(C₃₈H₂₄N₂= 508.62) 3-30 m/z = 449.12(C₃₂H₁₉NS = 449.57) 3-31 m/z =433.15(C₃₂H₁₉NO = 433.51) 3-32 m/z = 531.20(C₄₁H₂₅N = 531.66) 3-33 m/z =608.23(C₄₆H₂₈N₂ = 608.74) 3-34 m/z = 475.14(C₃₄H₂₁NS = 475.61) 3-35 m/z= 384.13(C₂₇H₁₆N₂O = 384.44) 3-36 m/z = 614.25(C₄₄H₃₀N₄ = 614.75) 3-37m/z = 508.19(C₃₈H₂₄N₂ = 508.62) 3-38 m/z = 449.12(C₃₂H₁₉NS = 449.57)3-39 m/z = 433.15(C₃₂H₁₉NO = 433.51) 3-40 m/z = 459.20(C₃₅H₂₅N = 459.59)3-41 m/z = 663.24(C₄₇H₂₉N₅ = 663.78) 3-42 m/z = 603.18(C₄₂H₂₅N₃S =603.74) 3-43 m/z = 587.20(C₄₂H₂₅N₃O = 587.68) 3-44 m/z = 613.25(C₄₅H₃₁N₃= 613.76) 3-45 m/z = 662.25(C₄₈H₃₀N₄ = 662.80) 3-46 m/z =577.16(C₄₀H₂₃N₃S = 577.71) 3-47 m/z = 601.18(C₄₂H₂₃N₃O₂ = 601.67) 3-48m/z = 759.27(C₅₇H₃₃N₃ = 759.91) 3-49 m/z = 586.22(C₄₂H₂₆N₄ = 586.70)3-50 m/z = 630.19(C₄₃H₂₆N₄S = 630.77) 3-51 m/z = 613.22(C₄₄H₂₇N₃O =613.72) 3-52 m/z = 639.27(C₄₇H₃₃N₃ = 639.80) 3-53 m/z = 508.19(C₃₈H₂₄N₂= 508.62) 3-54 m/z = 449.12(C₃₂H₁₉NS = 449.57) 3-55 m/z =433.15(C₃₂H₁₉NO = 43 3.51) 3-56 m/z = 609.25(C₄₇H₃₁N = 609.77) 3-57 m/z= 663.24(C₄₇H₂₉NS = 663.78) 3-58 m/z = 604.17(C₄₁H₂₄N₄S = 604.73) 3-59m/z = 587.20(C₄₂H₂₅N₃O = 587.68) 3-60 m/z = 613.2 5(C₄₅H₃₁N₃ = 613.76)3-61 m/z = 527.15(C₃₆H₂₁N₃S = 527.65) 3-62 m/z = 603.18(C₄₂H₂₅N₃S =605.74) 3-63 m/z = 516.20(C₃₆H₁₆D₅N₃O = 516.61) 3-64 m/z =605.23(C₄₃H₂₈FN₃ = 605.72) 3-65 m/z = 692.20(C₄₈H₂₈N₄S = 692.84) 3-66m/z = 577.16(C₄₀H₂₃N₃S = 577.71) 3-67 m/z = 561.18(C₄₀H₂₃N₃O = 561.64)3-68 m/z = 653.19(C₄₆H₂₇N₃S = 653.80) 3-69 m/z = 736.26(C₅₄H₃₂N₄ =736.88) 3-70 m/z = 677.19(C₄₈H₂₇N₃S = 677.83) 3-71 m/z =692.26(C₅₀H₂₄D₅N₃O = 692.83) 3-72 m/z = 743.24(C₅₃H₃₃N₃S = 743.93) 3-73m/z = 703.21(C₅₀H₂₉N₃S = 703.86) 3-74 m/z = 605.19(C₄₂H₂₇N₃S = 605.76)3-75 m/z = 735.18(C₅₀H₂₉N₃S₂ = 73 5.92) 3-76 m/z = 759.18(C₅₂H₂₉N₃S₂ =759.95) 3-77 m/z = 475.14(C₃₄H₂₁NS = 475.61) 3-78 m/z = 616.20(C₄₄H₂₈N₂S= 616.78) 3-79 m/z = 728.15(C₄₇H₂₅FN₄S₂ = 728.86) 3-80 m/z =818.25(C₅₈H₃₄N₄S = 819.00) 3-81 m/z = 603.18(C₄₂H₂₅N₃S = 603.74) 3-82m/z = 809.20(C₅₆H₃₁N₃S₂ = 810.01) 3-83 m/z = 659.15(C₄₄H₂₅N₃S₂ = 659.83)3-84 m/z = 623.24(C₄₃H₃₃N₃S = 623.82) 3-85 m/z = 844.27(C₆₀H₃₆N₄S =845.04) 3-86 m/z = 667.17(C₄₆H₂₅N₃OS = 667.79) 3-87 m/z =703.23(C₅₀H₂₉N₃O = 703.80) 3-88 m/z = 659.22(C₄₅H₂₉N₃O₃ = 659.75) 3-89m/z = 828.29(C₆₀H₃₆N₄O = 828.98) 3-90 m/z = 617.16(C₄₂H₂₃N₃OS = 617.73)3-91 m/z = 858.25(C₆₀H₃₄N₄OS = 859.02) 3-92 m/z = 792.26(C₅₅H₃₂N₆O =792.90) 3-93 m/z = 794.34(C₅₈H₄₂N₄ = 795.00) 3-94 m/z = 650.27(C₄₉H₃₄N₂= 650.83) 3-95 m/z = 878.30(C₆₄H₃₈N₄O = 879.04) 3-96 m/z =775.26(C₅₇H₃₃N₃O = 775.91) 3-97 m/z = 638.21(C₄₅H₂₆N₄O = 638.73) 3-98m/z = 511.17(C₃₆H₂₁N₃O = 511.58) 3-99 m/z = 601.18(C₄₂H₂₃N₃O₂ = 601.67)3-100 m/z = 740.26(C₅₃H₃₂N₄O = 740.87) 3-101 m/z = 577.16(C₄₀H₂₃N₃S =577.71) 3-102 m/z = 582.19(C₄₀H₁₈D₅N₃S = 582.74) 3-103 m/z =677.19(C₄₈H₂₇N₃S = 677.83) 3-104 m/z = 633.13(C₄₂H₂₃N₃S₂ = 633.79) 3-105m/z = 709.16(C₄₈H₂₇N₃S₂ = 709.89) 3-106 m/z = 667.17(C₄₆H₂₅N₃OS =667.79) 3-107 m/z = 693.19(C₄₈H₂₇N₃OS = 693.82) 3-108 m/z =727.21(C₅₂H₂₉N₃S = 727.89) 3-109 m/z = 723.14(C₄₈H₂₅N₃OS₂ = 723.9) 3-110m/z = 779.24(C₅₆H₃₃N₃S = 779.96) 3-111 m/z = 647.15(C₄₃H₂₅N₃S₂ = 647.81)3-112 m/z = 783.23(C₅₅H₃₃N₃OS = 783.95) 3-113 m/z = 848.21(C₅₈H₃₂N₄S₂ =849.04) 3-114 m/z = 691.21(C₄₉H₂₉N₃S = 691.85) 3-115 m/z =633.13(C₄₂H₂₃N₃S₂ = 633.79) 3-116 m/z = 767.20(C₅₄H₂₉N₃OS = 767.91)3-117 m/z = 733.22(C₅₁H₃₁N₃OS = 733.89) 3-118 m/z = 759.18(C₅₂H₂₉N₃S₂ =759.95) 3-119 m/z = 753.22(C₅₄H₃₁N₃S = 753.92) 3-120 m/z =527.15(C₃₆H₂₁N₃S = 527.65) 3-121 m/z = 532.18(C₃₆H₁₆N₃S = 532.68) 3-122m/z = 627.18(C₄₄H₂₅N₃S = 627.77) 3-123 m/z = 633.13(C₄₂H₂₃N₃S₂ = 633.79)3-124 m/z = 643.17(C₄₄H₂₅N₃OS = 643.76)

Otherwise, the synthesis examples of the present invention representedby Formulas (1) and (2) have been described, but these are all based onthe Buchwald-Hartwig cross coupling reaction, Suzuki cross-couplingreaction, Intramolecular acid-induced cyclization reaction (J. mater.Chem. 1999, 9, 2095.), Pd(II)-catalyzed oxidative cyclization reaction(Org. Lett. 2011, 13, 5504), Grignard reaction, Cyclic Dehydrationreaction and PPh3-mediated reductive cyclization reaction (J. Org. Chem.2005, 70, 5014.), and those skilled in the art will readily understandthat the above reaction proceeds even when, besides the substituentspecified in the specific synthesis example, other substituents(Substituents such as Ar¹ to Ar⁶, L¹ to L⁶, R¹ to R⁵, X¹, X², A and B)defined in Formula (1) and Formula (2) are bonded.

Evaluation of Manufacture of Organic Electric Element

Example 1) Manufacture and Evaluation of Red Organic Light EmittingDiode

(Emitting Layer Mixed Phosphorescent Host)

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) wasvacuum-deposited to form a hole injection layer with a thickness of 60nm, andN,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter will be abbreviated as NPB) was vacuum-deposited to form ahole transport layer with a thickness of 60 nm. On the hole transportlayer, a mixture of the compounds represented by Formulas (1) and (2)was used as a host in a ratio of 3:7, and as a dopant, an emitting layerwith a thickness of 30 nm was deposited on the hole transport layer bydoping (piq)₂Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] with a weight of5%. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAlq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and tris(8-quinolinol)aluminum(hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nmas an electron transport layer. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

[Example 2] to [Example 58] Red Organic Light Emitting Diode

(Emitting Layer Mixed Phosphorescent Host)

The inventive compound represented by Formula (1) and Formula (2) of thepresent invention as the host material of the emitting layer wasprepared in the same manner as in Example 1 to prepare an organicelectroluminescent device, except for using the compounds of the presentinvention described in Table 7 below,

Comparative Examples 1 to 3

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the compound represented by Formula (2) wasused as a host alone.

Comparative Example 4

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 1 was used as ahost alone.

Comparative Example 5

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 2 was used as ahost alone.

Comparative Example 6

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 3 was used as ahost alone.

Comparative Example 7

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the comparative compound 4 was used as ahost alone.

Comparative Example 8

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that comparative compound 1 and 2 were mixed andused as a host.

Comparative Example 9

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that comparative compound 3 and 4 were mixed andused as a host.

To the OLEDs which were manufactured by example 1 to 58 and comparativeexamples 1 to 9, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of2500 cd/m². The measurement results are shown in Tables 7 and 8 below.

When the second host is fixed and various first hosts are mixed.

TABLE 7 Current Brightness Efficiency Lifetime First host Second hostVoltage Density (cd/m²) (cd/A) T(95) comparative — compound (3-6) 6.317.9 2500 14.0 105.7 example (1) comparative — compound (3- 6.5 18.22500 13.7 104.2 example (2) 61) comparative — compound (3- 6.6 18.9 250013.2 101.6 example (3) 74) comparative — comparative 7.1 20.4 2500 12.380.3 example (4) compound 1 comparative — comparative 7 20 2500 12.581.9 example (5) compound 2 comparative — comparative 6.9 19.5 2500 12.885.4 example (6) compound 3 comparative — comparative 7.1 20.2 2500 12.480.9 example (7) compound 4 comparative comparative comparative 6.2 132500 19.3 102.8 example (8) compound 1 compound 2 comparativecomparative comparative 6 12.4 2500 20.1 105.9 example (9) compound 3compound 4 example (1) compound compound 3-6 4.4 7.8 2500 32.2 133.4 1-3example (2) compound compound 3-6 4.7 9.1 2500 27.5 124.8 1-5 example(3) compound compound 3-6 4.6 8.8 2500 28.4 128.7 1-10 example (4)compound compound 3-6 4.5 9.4 2500 26.7 125.6 1-15 example (5) compoundcompound 3-6 4.5 9.0 2500 27.7 129.5 1-16 example (6) compound compound3-6 4.5 9.8 2500 25.6 126.8 1-19 example (7) compound compound 3-6 4.47.3 2500 34.1 130.5 2-1 example (8) compound compound 3-6 4.5 7.7 250032.6 128.3 2-5 example (9) compound compound 3-6 4.6 8.8 2500 28.3 126.62-6 example (10) compound compound 3-6 4.6 9.1 2500 27.4 124.8 2-10example (11) compound compound 3-6 4.7 8.2 2500 30.4 127.5 2-14 example(12) compound compound 3-6 4.7 8.9 2500 28.1 125 2-15 example (13)compound compound 3-6 4.7 9.4 2500 26.7 124.5 2-18 example (14) compoundcompound 3-6 4.5 8.8 2500 28.4 123.1 2-26 example (15) compound compound3-6 4.7 9.2 2500 27.1 123.4 2-36 example (16) compound compound 3-6 4.78.9 2500 28.2 121.7 2-63 example (17) compound compound 3-6 4.6 9.1 250027.4 124.2 2-65 example (17′) compound compound 3-6 4.3 7.8 2500 32.0138.4 2-76

When the first host material and various second host materials aremixed.

TABLE 8 Second Current Brightness Efficiency Lifetime First host hostVoltage Density (cd/m²) (cd/A) T(95) example (18) compound compound 4.59.1 2500 27.5 130.1 1-3 3-7 example (19) compound 4.5 8.7 2500 28.8131.5 3-8 example (20) compound 4.5 10.0 2500 25.1 123.7 3-15 example(21) compound 4.6 10.7 2500 23.3 124.3 3-37 example (22) compound 4.59.7 2500 25.7 127.1 3-46 example (23) compound 4.6 9.8 2500 25.6 125.53-50 example (24) compound 4.4 8.2 2500 30.4 131.7 3-61 example (25)compound 4.5 8.4 2500 29.8 130.4 3-74 example (26) compound 4.5 9.5 250026.2 126.7 3-81 example (27) compound 4.5 10.3 2500 24.2 123 3-90example (28) compound 4.6 11.3 2500 22.1 121.4 3-100 example (29)compound compound 4.6 9.1 2500 27.4 129.0 1-10 3-7 example (30) compound4.6 8.6 2500 29.1 132.6 3-8 example (31) compound 4.6 10.1 2500 24.9122.1 3-15 example (32) compound 4.7 10.4 2500 24.0 123.3 3-37 example(33) compound 4.6 9.7 2500 25.8 124.5 3-46 example (34) compound 4.710.0 2500 24.9 124.9 3-50 example (35) compound 4.5 8.2 2500 30.5 130.63-61 example (36) compound 4.6 8.8 2500 28.3 129.4 3-74 example (37)compound 4.6 10.8 2500 23.3 121.8 3-90 example (38) compound 4.6 11.72500 21.4 119.9 3-100 example (39) compound compound 4.4 8.9 2500 28.2125.2 2-1 3-7 example (40) compound 4.4 9.1 2500 27.5 127.4 3-8 example(41) compound 4.4 9.9 2500 25.2 121.5 3-15 example (42) compound 4.611.3 2500 22.1 120.4 3-37 example (43) compound 4.4 9.4 2500 26.5 126.33-46 example (44) compound 4.5 10.5 2500 23.8 121.8 3-50 example (45)compound 4.4 8.2 2500 30.4 127.3 3-61 example (46) compound 4.5 9.8 250025.6 124.5 3-74 example (47) compound 4.5 10.1 2500 24.8 122.2 3-90example (48) compound 4.5 11.0 2500 22.7 121.7 3-100 example (49)compound compound 4.5 9.4 2500 26.6 124.2 2-14 3-7 example (50) compound4.5 9.9 2500 25.3 124.7 3-8 example (51) compound 4.6 11.1 2500 22.5121.4 3-15 example (52) compound 4.7 12.2 2500 20.5 119.3 3-37 example(53) compound 4.5 10.2 2500 24.5 122.7 3-46 example (54) compound 4.611.3 2500 22.1 120.5 3-50 example (55) compound 4.5 9.1 2500 27.6 126.03-61 example (56) compound 4.6 9.7 2500 25.7 125.2 3-74 example (57)compound 4.6 10.7 2500 23.4 123.5 3-90 example (58) compound 4.6 11.52500 21.7 121.8 3-100 example (58′) compound compound 4.5 7.8 2500 32.8137.9 2-76 3-101

As can be seen from the results of Table 7 and 8, when the organicelectric element material of the present invention represented byFormulas (1) and (2) is mixed and used as a phosphorescent host(Examples 1 to 58), it was confirmed that the driving voltage,efficiency, and life span were significantly improved as compared withthe element using a single material (comparative examples 1 to 7).

More specifically, in Comparative Examples 1 to 7, wherein the compoundsof the present invention represented by Formula (2) and comparativecompounds 1 to 4 are used alone as a phosphorescent host, ComparativeExamples 1 to 3 using the compounds (3-6, 3-61, and 3-74) of the presentinvention had higher efficiency and longer life span than ComparativeExamples 4 to 7 using the comparative compound.

Also, Comparative Example 8 and 9 wherein Comparative Compound 1 and 2or Comparative Compound 3 and 4 were mixed and used as a phosphorescenthost were found to exhibit higher efficiency than Comparative Examples 1to 7 using the single substance.

Comparing Comparative Example 8 with 9, Comparative Example 9 using amixture containing a polycyclic compound having a different heteroatom(N, S) among the 5-membered compounds had higher efficiency thanComparative Example 8 mixed a 5-membered heterocyclic compound havingthe same nitrogen atom.

And it was confirmed that Example 1 to 58 using the mixture of thecompound of Formula (1) and (2) as a host exhibited remarkably highefficiency and long life span than the Comparative Example 1 to 9.

On the basis of the above experimental results, the inventors of thepresent invention have found that, in the case of a mixture of thesubstance of Formulas (1) and (2), they have novel characteristics otherthan those for the respective materials, and have measured the PLlifetime using the substance of Formula (1), the substance of Formula(2), and the mixture of the present invention. As a result, it wasconfirmed that a new PL wavelength was formed when the compounds ofFormulas (1) and (2) were mixed, and the decreasing and disappearingtime of the newly formed PL wavelength increased from about 60 times toabout 360 times compared to the reduction and disappearance times ofsubstances Formula (1) and (2), respectively. It is considered whenmixed with the compound of the present invention, not only electrons andholes are moved through the energy level of each substance, but also theefficiency and life span are increased by electron, hole transport orenergy transfer by a new region (exciplex) having a new energy levelformed due to mixing. As a result, when the mixture of the presentinvention is used, the mixed thin film is an important example showingexciplex energy transfer and light emitting process.

The reason why the combination of the present invention is superior toComparative Examples 8 to 9 in which a comparative compound is used as aphosphorescent host is that the high T1 and high LUMO energy valuesimprove the electron blocking ability and allow more holes to be movedto the emitting layer more quickly and easily when a compoundrepresented by Formula (1) having a strong hole property is mixed with apolycyclic compound represented by Formula (2), which is characterizednot only by electron but also by hole stability and high T1. As aresult, the charge balance in the emitting layer of holes and electronsis increased, so that light emission is well performed inside theemitting layer rather than at the interface of the hole transport layer,and therefore the deterioration in the HTL interface is also reduced,thereby maximizing the driving voltage, efficiency and life span of thedevice. Among the compounds represented by Formula (1), 1) when Ar¹ andAr² are of the type in which the ring is curled, it has been confirmedthat compounds having at least one of Ar³ and Ar⁴ substituted withbiphenyl exhibits the best results in terms of the driving voltage, theefficiency and the lifetime, and compounds having at least one of Ar³and Ar⁴ substituted with Dibenzothiophen or Dibenzofuran were found tobe excellent in efficiency and lifetime, and in the case of compounds inwhich at least one of Ar³ and Ar⁴ is substituted with fluorene, thedriving voltage is excellent. 2) When Ar¹ and Ar² do not form a ring,compounds in which both Ar³ and Ar⁴ were substituted with naphthylshowed the best results in terms of driving voltage, efficiency, andlifetime, and compounds having at least one of Ar³ and Ar⁴ substitutedwith Dibenzothiophen or Dibenzofuran were confirmed to have excellentefficiency and lifetime.

That is, it is concluded that the combination of Formula (1) and Formula(2) is electrochemically synergistic to improve the performance of thedevice as a whole.

Also, Table 8 shows the results obtained using Table 7, in which a firsthost with high performance was fixed and a variety of second hosts weremixed. As a result, as the first host, when compounds 1-3, 1-10, 2-1 and2-14 having the best driving voltage, efficiency, and lifetime and, asthe second host, the compounds 3-7, 3-8, 3-9, 3-15, 3-37, 3-46, 3-50,3-61, 3-74, 3-90 and 3-100 were mixed, it can be seen that the drivingvoltage, efficiency and lifetime can be remarkably improved by using twomixed host materials as compared with the case of using a single hostmaterial.

[Example 59] to [Example 66] Manufacture and Evaluation of Red OrganicLight Emitting Diode by Mixing Ratio

An organic electroluminescent device was manufactured in the same manneras in Example 1, except that the materials are used in different mixingratios as listed in Table 9.

TABLE 9 Mixing ratio (fist Current Second host:second Density BrightnessEfficiency First host host host) Voltage (mA/cm²) (cd/m²) (cd/A) T(95)example (59) compound compound 2:8 4.4 8.6 2500 29.2 131.6 1-3 3-6example (60) 3:7 4.4 7.9 2500 31.8 133.2 example (61) 4:6 4.8 9.1 250027.4 127.6 example (62) 5:5 4.9 10.1 2500 24.8 121.7 example (63)compound compound 2:8 4.5 7.9 2500 31.5 129.8 2-1 3-61 example (64) 3:74.4 8.1 2500 30.7 127.5 example (65) 4:6 4.8 9.3 2500 26.9 124.3 example(66) 5:5 5.0 10.7 2500 23.4 116.8

As shown in Table 9, the mixture of the compound of the presentinvention was measured by fabricating the device in (2:8, 3:7, 4:6,5:5). To explain the results in detail, in the result of the mixture ofthe compound 1-3 and 3-6, the results of the driving voltage, theefficiency and the life span were similarly excellent at 2:8 and 3:7,but as the ratio of the first host increases, such as 4:6 and 5:5, theresults of the driving voltage, the efficiency and the life span aregradually decreased, this was also the same in the result of the mixtureof the compound 2-1 and 3-61. This can be explained by the fact that thecharge balance in the emitting layer is maximized when an appropriateamount of the compound represented by Formula (1) having strong holeproperties such as 2:8 and 3:7 is mixed.

3) Addition of Emitting Auxiliary Layer+Phosphorescent Host ElementResult

[Example 67] to [Example 82] Manufacture and Evaluation of Red OrganicLight Emitting Diode (Formula (1): Hole Transport Layer, Formula (2):Phosphorescent Host)

First, on an ITO layer (anode) formed on a glass substrate,N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter will be abbreviated as 2-TNATA) wasvacuum-deposited to form a hole injection layer with a thickness of 60nm, andN,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine(hereinafter will be abbreviated as NPB) was vacuum-deposited to form ahole transport layer with a thickness of 60 nm. Subsequently, theinventive compound represented by Formula (1) was vacuum-deposited as anemitting auxiliary layer material to a thickness of 20 nm to form anemitting auxiliary layer. After forming the emitting auxiliary layer,the compound of the present invention represented by Formula (2) wasused in the upper portion of the emitting auxiliary layer, and as adopant, an emitting layer with a thickness of 30 nm was deposited on thehole transport layer by doping (piq)₂Ir(acac)[bis-(1-phenylisoquinolyl)iridium(III)acetylacetonate] with a weight of95:5. (1,1′-bisphenyl)-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter abbreviated as BAlq) was vacuum deposited as a holeblocking layer to a thickness of 10 nm, and tris(8-quinolinol)aluminum(hereinafter abbreviated as Alq3) was deposited to a thickness of 40 nmas an electron transport layer. After that, an alkali metal halide, LiFwas vacuum deposited as an electron injection layer to a thickness of0.2 nm, and Al was deposited to a thickness of 150 nm to form a cathodeto manufacture an OLED.

To the OLEDs which were manufactured by examples and comparativeexamples, a forward bias direct current voltage was applied, andelectroluminescent (EL) properties were measured using PR-650 ofPhotoresearch Co., and T95 life was measured using a life measuringapparatus manufactured by McScience Inc. with a reference luminance of2500 cd/m². In the following table, the manufacture of a device and theresults of evaluation are shown.

[Comparative Example 10] to [Comparative Example 13]

An organic electroluminescent device was fabricated in the same manneras in the previous example, except that the emitting auxiliary layer wasnot used.

TABLE 10 Emitting auxiliary layer phosphorescent Current BrightnessLifetime compound host material Voltage Density (cd/m²) Efficiency T(95)comparative compound 3-6 6.3 17.9 2500.0 14.0 105.7 example (10)comparative compound 3-61 6.5 18.2. 2500.0 13.7 104.2 example (11)comparative compound 3- 6.6 18.9 2500.0 13.2 101.6 example (12) 74comparative compound 3- 6.2 16.0 2500.0 15.6 110.1 example (13) 101example (67) compound compound 3-6 5.9 12.7 2500.0 19.7 117.1 example(68) 2-1 compound 3-61 5.9 13.0 2500.0 19.2 117.3 example (69) compound3- 6.0 13.7 2500.0 18.3 115.1 74 example (70) compound 3- 5.8 11.32500.0 22.1 120.4 101 example (71) compound compound 3-6 5.4 8.0 2500.031.3 132.0 example (72) 2-76 compound 3-61 5.4 7.9 2500.0 31.7 132.9example (73) compound 3- 5.5 8.3 2500.0 30.3 130.6 74 example (74)compound 3- 5.4 7.7 2500.0 32.4 135.4 101 example (75) compound compound3-6 5.5 9.0 2500.0 27.8 127.5 example (76) 2-88 compound 3-61 5.6 8.92500.0 28.1 127.1 example (77) compound 3- 5.6 9.5 2500.0 26.2 125.2 74example (78) compound 3- 5.5 8.1 2500.0 30.7 130.6 101 example (79)compound compound 3-6 5.7 10.8 2500.0 23.2 122.8 example (80) 2-106compound 3-61 5.7 10.4 2500.0 24.1 122.1 example (81) compound 3- 5.811.2 2500.0 22.4 120.4 74 example (82) compound 3- 5.6 9.5 2500.0 26.3125.1 101

As can be seen from the results of Table 10, when a compound representedby Formula (1) is used as a material for the emitting auxiliary layerand a compound represented by Formula (2) is used as a material for theemitting layer, the driving voltage of the organic electroluminescentdevice can be lowered and the luminous efficiency and lifetime can beremarkably improved as compared with the comparative example not usingthe emitting auxiliary layer.

In general, there is an injection barrier between HTL and EML, so thatthe hole can not be transferred easily, and the charge balance is notmatched so that the driving voltage is increased. Therefore, it isconsidered that the charge balance of the hole and electron in theemitting layer is adjusted by the introduction of the emitting auxiliarylayer having a proper HOMO level between HTL and EML.

Specially, a compound in which at least one of Ar¹, Ar², Ar³, Ar⁴, L¹,L², L³, L⁴, and L⁵ is substituted with a dibenzothiophene ordibenzofuran exhibited remarkably higher refractive index and higher Tgas compared with the case where the general aryl group was substituted,so that the efficiency and the thermal stability were improved, and itwas judged that the compound showed improved device results.

The compound of the present invention represented by Formula (1)suitably align the barriers of HTL and EML so that the device has afeature of high hole mobility, and compounds of the present inventionrepresented by Formula (2) have characteristics of hole stability, fastelectron mobility and high T1. Therefore, the combination of theseincreases the charge balance in the emitting layer, so that lightemission is well performed inside the emitting layer rather than at theinterface of the hole transport layer, and therefore the deteriorationin the ITO and HTL interface is also reduced, thereby maximizing thedriving voltage, efficiency and life span of the device. That is, it isjudged that the combination of the compound of the present inventionrepresented by Formula (1) and the compound of the present inventionrepresented by Formula (2) is electrochemically synergistic to improvethe performance of the device as a whole.

Although exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art willappreciate that various modifications, additions and substitutions arepossible, without departing from the scope and spirit of the inventionas disclosed in the accompanying claims. Therefore, the embodimentdisclosed in the present invention is intended to illustrate the scopeof the technical idea of the present invention, and the scope of thepresent invention is not limited by the embodiment.

The scope of the present invention shall be construed on the basis ofthe accompanying claims, and it shall be construed that all of thetechnical ideas included within the scope equivalent to the claimsbelong to the present invention.

What is claimed is:
 1. An organic electric element comprising a firstelectrode, a second electrode, and an organic material layer formedbetween the first electrode and the second electrode, wherein theorganic material layer comprises an emitting layer and the emittinglayer comprises a first host compound represented by Formula (1) and asecond host compound represented by Formula (2) as a phosphorescentlight emitting layer:

wherein: 1) Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are each independently selectedfrom the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S,Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b)); and Ar¹ and Ar² or Ar³ and Ar⁴ may be bonded toeach other to form a ring, 2) c and e are an integer of 0 to 10, and dis an integer of 0 to 2, 3) R³, R⁴ and R⁵ are the same or different fromeach other, and are each independently selected from the groupconsisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxygroup; and -L′-N(R_(a))(R_(b)); or in case c, d and e are 2 or more, andR³, R⁴ and R⁵ are each in plural being the same or different, and aplurality of R³ or a plurality of R⁴ or a plurality of R⁵ may be bondedto each other to form a ring; 4) L¹, L², L³, L⁴, L⁵ and L⁶ are eachindependently selected from the group consisting of a single bond; aC₆-C₆₀ arylene group; and a fluorenylene group; a fused ring group of aC₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group; provided that except when L⁵ is a single bond, 5) Aand B are each independently a C₆-C₂₀ aryl group or a C₂-C₂₀heterocyclic group, provided that when both A and B are a substituted orunsubstituted C₆ aryl group (phenyl group), d is 2, and R⁴s are bondedto each other to form an aromatic or heterocyclic group, 6) i and j areeach 0 or 1 with the proviso that i+j is 1 or more, and when i or j is0, it means a direct bond, 7) X¹ and X² are each independently N-L⁷-Ar⁶,O, S, or CR⁶R⁷, wherein L⁷ is the same as L¹ to L⁴ or L⁶ defined, Ar⁶ isthe same as Ar¹ to Ar⁵ defined, and R⁶ and R⁷ are each independentlyhydrogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀ heterocyclicgroup; or a C₁-₅₀ alkyl group and R⁶ and R⁷ may combine to each other toform a spiro, and 8) L′ is selected from the group consisting of asingle bond; a C₆-C₆₀ arylene group; a fluorenylene group; a fused ringgroup of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and aC₂-C₆₀ heterocyclic; and R_(a) and R_(b) are each independently selectedfrom the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; afused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring;and a C₂-C₆₀ heterocyclic group containing at least one hetero atom ofO, N, S, Si, or P, wherein, the aryl group, fluorenyl group, arylenegroup, heterocyclic group, fluorenylene group, fused ring group, alkylgroup, alkenyl group, alkoxy group and aryloxy group may be substitutedwith one or more substituents selected from the group consisting ofdeuterium; halogen; a silane group substituted or unsubstituted withC₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxane group; boron group;germanium group; cyano group; nitro group; -L′-N(R_(a))(R_(b)); a C₁-C₂₀alkylthio group; C₁-C₂₀ alkoxyl group; C₁-C₂₀ alkyl group; C₂-C₂₀alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀ aryl group; C₆-C₂₀ arylgroup substituted with deuterium; a fluorenyl group; C₂-C₂₀ heterocyclicgroup; C₃-C₂₀ cycloalkyl group; C₇-C₂₀ arylalkyl group; and C₈-C₂₀)arylalkenyl group; wherein the substituents may combine each other andform a saturated or unsaturated ring, wherein the term ‘ring’ meansC₃-C₆₀ aliphatic ring or C₆-C₆₀ aromatic ring or a C₂-C₆₀ heterocyclicgroup or a fused ring formed by the combination of thereof and includesa saturated or unsaturated ring.
 2. The organic electric elementaccording to claim 1, comprising a compound represented by the followingFormula (3) when Ar¹ and Ar² in Formula (1) form a ring;

wherein: 1) L³, L⁴, L⁵, Ar³ and Ar⁴ are the same as defined in claim 1,2) a and b are each independently an integer of 0 to 4, 3) R¹ and R² arethe same or different from each other, and are each independentlyselected from the group consisting of hydrogen; deuterium; halogen; aC₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₂₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P; a fused ringgroup of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀ aromatic ring; a C₁-C₂₀alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₂₀alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or incase a and b are 2 or more, R¹ and R² are each in plural being the sameor different, and a plurality of R¹ or a plurality of R² may be bondedto each other to form a ring.
 3. The organic electric element accordingto claim 1, wherein L¹, L², L³, L⁴ and L⁵ in Formula (1) are eachindependently any one of the following Formulas (A-1) to (A-13):

wherein: 1) a′, c′, d′ and e′ are an integer of 0 to 4; and b′ is aninteger of 0 to 6; and f′ and g′ are an integer of 0 to 3; and h′ is aninteger of 0 or 1; and i′ is an integer of 0 to 2, and j′ is an integerof 0 to 4, 2) R⁸, R⁹, R¹⁰ and R¹⁵ are the same or different from eachother, and are each independently selected from the group consisting ofhydrogen; deuterium; halogen; a C₆-C₂₀ aryl group; a fluorenyl group; aC₂-C₂₀ heterocyclic group including at least one heteroatom of O, N, S,Si or P; a fused ring group of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀aromatic ring; a C₁-C₂₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₂₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b)); wherein e′, f′, g′, i′ and j′ are 2 or more, R⁸,R⁹, R¹⁰ and R¹⁵ are each in plural being the same or different, and aplurality of R⁸ or a plurality of R⁹ or a plurality of R¹⁰ or aplurality of R¹⁵, two adjacent R⁸ and R⁹, or R⁹ and R¹⁰, or R¹⁰ and R¹⁵may be bonded to form an aromatic ring or heteroaromatic ring, 3) Y isN-L⁸-Ar⁷, O, S or CR¹¹R¹², wherein L⁸ is the same as L¹ to L⁶ defined inclaim 1, Ar⁷ is the same as Ar¹ to Ar⁵ defined in claim 1, and R¹¹ andR¹² are the same as R⁶ and R⁷ defined in claim 1, 4) Z¹, Z² and Z³ areeach CR¹³ or N, and at least one of Z¹, Z² and Z³ is N, and R¹³ is thesame as R⁸ and R¹⁰ defined above.
 4. The organic electric elementaccording to claim 1, wherein the first host compound represented byFormula (1) is represented by any one of the following Formulas (3-1) to(3-19):

wherein: L³, L⁴, L⁵, Ar³ and Ar⁴ are the same as defined in claim 1, 1)a and b are each independently integer of 0 to 4, 2) R¹, R², R⁸ and R⁹are the same or different from each other, and are each independentlyselected from the group consisting of hydrogen; deuterium; halogen; aC₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₂₀ heterocyclic groupincluding at least one heteroatom of O, N, S, Si or P; a fused ringgroup of a C₃-C₂₀ aliphatic ring and a C₆-C₂₀ aromatic ring; a C₁-C₂₀alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynyl group; a C₁-C₂₀alkoxyl group; a C₆-C₃₀ aryloxy group; and -L′-N(R_(a))(R_(b)); or incase a, b, a′, d′, f′ or g′ are 2 or more, R¹, R², R⁸ and R⁹ are each inplural being the same or different, and a plurality of R¹ or a pluralityof R² or a plurality of R⁸ or a plurality of R⁹, or adjacent R¹ and R²,or R⁸ and R⁹ may be bonded to each other to form an aromatic orheteroaromatic ring, 3) a′ and d′ are an integer of 0 to 4; and f′ andg′ are an integer of 0 to 3; 4) Y is N-L⁸-Ar⁷, O, S or CR¹¹R¹², 5) W isN-L⁸-Ar⁷, O, S or CR¹¹R¹², wherein L⁸ is the same as L¹ to L⁶ defined inclaim 1, Ar⁷ is the same as Ar¹ to Ar⁵ defined in claim 1, and R¹¹ andR¹² are the same as R⁶ and R⁷ defined in claim
 1. 5. The organicelectric element according to claim 1, wherein both Ar³ and Ar⁴ inFormula (1) are a C₆-C₂₄ aryl group.
 6. The organic electric elementaccording to claim 1, wherein at least one of Ar³ and Ar⁴ in Formula (1)is a dibenzothiophene or dibenzofuran compound.
 7. The organic electricelement according to claim 1, wherein at least one of L¹, L², L³, L⁴ andL⁵ in Formula (1) is substituted in m (meta)-position.
 8. The organicelectric element according to claim 1, wherein the first host compoundrepresented by Formula (1) is represented by Formula (3-20):

wherein: Ar¹, Ar², Ar³, Ar⁴, L¹, L², L³ and L⁴ are the same as definedin claim 1, 1) R⁸ and R⁹ are the same or different from each other, andare each independently selected from the group consisting of hydrogen;deuterium; halogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group including at least one heteroatom of O, N, S, Si orP; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromaticring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀ alkynylgroup; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b)); or f′ and g′ are 2 or more, R⁸ and R⁹ are each inplural being the same or different, and a plurality of R⁸ or a pluralityof R⁹, or two adjacent R⁸ and R⁹ may be bonded to form an aromatic orheteroaromatic ring, 2) f′ and g′ are integer of 0 to
 3. 9. The organicelectric element according to claim 1, wherein the second host compoundrepresented by Formula (2) is represented by the following Formula (4)or (5):

wherein R³, R⁴, R⁵, L⁶, Ar⁵, X¹, X², A, B, c, d, and e are the same asdefined in claim
 1. 10. The organic electric element according to claim1, wherein A and B in Formula (2) are selected from the group consistingof the following Formulas (B-1) to (B-7):

wherein: 1) Z⁴ to Z⁵⁰ are CR¹⁴ or N, 2) R¹⁴ is the same as R³ to R⁵defined in claim 1, 3) * indicates the position to be condensed.
 11. Theorganic electric element according to claim 1, wherein the second hostcompound represented by Formula (2) comprises a compound represented byany of the following Formulas (4-1) to (4-35):

wherein: X¹, X², L⁶, Ar⁵, R³, R⁴ and R⁵, are the same as defined inclaim 1, c and e are each independently any one of integers of 0 to 8, dis any one of integers of 0 to
 4. 12. The organic electric elementaccording to claim 1, wherein the second host compound represented byFormula (2) comprises a compound represented by any of the followingFormulas (6-1) to (6-8):

wherein R³, R⁴, R⁵, R⁶, R⁷, L⁶, L⁷, Ar⁵, Ar⁶, c, d, e, A and B are thesame as defined in claim
 1. 13. The organic electric element accordingto claim 1, wherein the first host compound represented by Formula (1)comprises any of the following Compounds 1-1 to 1-60 and 2-1 to 2-106:


14. The organic electric element according to claim 1, wherein thesecond host compound represented by Formula (2) comprises any one of thefollowing Compounds 3-1 to 3-124:


15. The organic electric element of claim 1, further comprising at leastone hole transporting band layer between the first electrode and theemitting layer, wherein the hole transporting band layer comprises ahole transport layer, an emitting auxiliary layer, or both the layers,and the hole transporting band layer comprises a compound represented byFormula (1).
 16. The organic electric element according to claim 1,wherein the compounds represented by Formula (1) and (2) are mixed inratio of 1:9 to 9:1 to be included in the emitting layer.
 17. Theorganic electric element according to claim 1, wherein the compoundsrepresented by Formula (1) and (2) are mixed in a ratio of 2:8 or 3:7 tobe included in the emitting layer.
 18. A display device comprising theorganic electric element of claim 1; and a control part driving thedisplay device.
 19. A display device according to claim 18, wherein theorganic electric element is at least one of an OLED, an organic solarcell, an organic photo conductor(OPC), organic transistor(organic TFT)and an element for monochromic or white illumination.
 20. An organicelectric element comprising; a first electrode; a second electrode; andan organic material layer disposed between the first electrode and thesecond electrode and comprising at least an emitting auxiliary layer andan emitting layer, wherein the emitting auxiliary layer comprises acompound represented by Formula (3-20) and the emitting layer comprisesa compound represented by Formula (2):

wherein: 1) Ar¹, Ar², Ar³, Ar⁴ and Ar⁵ are each independently selectedfrom the group consisting of a C₆-C₆₀ aryl group; a fluorenyl group; aC₂-C₆₀ heterocyclic group including at least one hetero atom of O, N, S,Si or P; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenyl group; a C₂-C₂₀alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxy group; and-L′-N(R_(a))(R_(b)); and neither Ar¹ and Ar² nor Ar³ and Ar⁴ are bondedto each other to form a ring, 2) c and e are an integer of 0 to 10, andd is an integer of 0 to 2, 3) R³, R⁴ and R⁵ are the same or differentfrom each other, and are each independently selected from the groupconsisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkynyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxygroup; and -L′-N(R_(a))(R_(b)); or in case c, d and e are 2 or more, andR³, R⁴ and R⁵ are each in plural being the same or different, and aplurality of R³ or a plurality of R⁴ or a plurality of R⁵ may be bondedto each other to form a ring; R⁸ and R⁹ are the same or different fromeach other, and are each independently selected from the groupconsisting of hydrogen; deuterium; halogen; a C₆-C₆₀ aryl group; afluorenyl group; a C₂-C₆₀ heterocyclic group including at least oneheteroatom of O, N, S, Si or P; a fused ring group of a C₃-C₆₀ aliphaticring and a C₆-C₆₀ aromatic ring; a C₁-C₅₀ alkyl group; a C₂-C₂₀ alkenylgroup; a C₂-C₂₀ alkenyl group; a C₁-C₃₀ alkoxyl group; a C₆-C₃₀ aryloxygroup; and -L′-N(R_(a))(R_(b)); or f′ and g′ are 2 or more, R⁸ and R⁹are each in plural being the same or different, and a plurality of R⁸ ora plurality of R⁹, or two adjacent R⁸ and R⁹ may be bonded to form anaromatic or heteroaromatic ring, and 4) L¹, L², L³, L⁴, L⁵ and L⁶ areeach independently selected from the group consisting of a single bond;a C₆-C₆₀ arylene group; and a fluorenylene group; a fused ring group ofa C₃-C₆₀ aliphatic ring and a C₆-C₆₀ aromatic ring; and a C₂-C₆₀heterocyclic group; provided that except when L⁵ is a single bond, 5) Aand B are each independently a C₆-C₂₀ aryl group or a C₂-C₂₀heterocyclic group, with the proviso that both A and B are not C₆-arylgroup at the same time, 6) i and j are each 0 or 1 with the proviso thati+j is 1 or more, and when i or j is 0, it means a direct bond, f′ andg′ are each an integer of 0 to 3, 7) X¹ and X² are each independentlyN-L⁷-Ar⁶, O, S, or CR⁶R⁷, wherein L⁷ is the same as L¹ to L⁴ or L⁶defined, Ar⁶ is the same as Ar¹ to Ar⁵ defined, and R⁶ and R⁷ are eachindependently hydrogen; a C₆-C₆₀ aryl group; a fluorenyl group; a C₂-C₆₀heterocyclic group; or a C₁-C₅₀ alkyl group and R⁶ and R⁷ may combine toeach other to form a spiro, and 8) L′ is selected from the groupconsisting of a single bond; a C₆-C₆₀ arylene group; a fluorenylenegroup; a fused ring group of a C₃-C₆₀ aliphatic ring and a C₆-C₆₀aromatic ring; and a C₂-C₆₀ heterocyclic; and Ra and Rb are eachindependently selected from the group consisting of a C₆-C₆₀ aryl group;a fluorenyl group; a fused ring group of a C₃-C₆₀ aliphatic ring and aC₆-C₆₀ aromatic ring; and a C₂-C₆₀ heterocyclic group containing atleast one hetero atom of O, N, S, Si, or P, wherein, the aryl group,fluorenyl group, arylene group, heterocyclic group, fluorenylene group,fused ring group, alkyl group, alkenyl group, alkoxy group and aryloxygroup may be substituted with one or more substituents selected from thegroup consisting of deuterium; halogen; a silane group substituted orunsubstituted with C₁-C₂₀ alkyl group or C₆-C₂₀ aryl group; siloxanegroup; boron group; germanium group; cyano group; nitro group;-L′-N(R_(a))(R_(b)); a C₁-C₂₀ alkylthio group; C₁-C₂₀ alkoxyl group;C₁-C₂₀ alkyl group; C₂-C₂₀ alkenyl group; C₂-C₂₀ alkynyl group; C₆-C₂₀aryl group; C₆-C₂₀ aryl group substituted with deuterium; a fluorenylgroup; C₂-C₂₀ heterocyclic group; C₃-C₂₀ cycloalkyl group; C₇-C₂₀arylalkyl group; and Cs-Ca) arylalkenyl group; wherein the substituentsmay combine each other and form a saturated or unsaturated ring, whereinthe term ‘ring’ means C₃-C₆₀ aliphatic ring or C₆-C₆₀ aromatic ring or aC₂-C₆₀ heterocyclic group or a fused ring formed by the combination ofthereof and includes a saturated or unsaturated ring.
 21. A displaydevice comprising the organic electric element of claim 20; and acontrol part driving the display device.
 22. A display device accordingto claim 21, wherein the organic electric element is at least one of anOLED, an organic solar cell, an organic photo conductor(OPC), organictransistor(organic TFT) and an element for monochromic or whiteillumination.